Genetic characterization of 2 Ceutorhynchus (Coleoptera: Curculionidae) weevils with mitogenomes and insights into the phylogeny and evolution of related weevils.

The rape stem weevil (Ceutorhynchus asper Roel.) and its close relatives primarily breed on cruciferous plants and cause severe damage to rapeseed production. However, their genetic and molecular information is still scarce. Here, we generated mitogenomes for both C. asper and Ceutorhynchus albosuturalis. The lengths of the 2 mitochondrial genomes are 14,207 bp (C. asper) and 15,373 bp (C. albosuturalis), and both weevils exhibit identical numbers of protein-coding genes with the absence of trnI. A + T contents for both mitogenomes are high (80% and 79.9%, respectively). Haplotype and genetic distance analyses showed that the genetic differentiation of C. asper populations in northwestern China is low. Based on 5 datasets from mitogenomes, phylogenetic analyses with maximum-likelihood and Bayesian methods show that both species (C. asper and C. albosuturalis) fall in the CCCMS clade (Curculioninae, Conoderinae, Cossoninae, Molytinae, and Scolytinae) of Curculionidae and belong to clades H and I of the genus Ceutorhynchus, respectively. Larvae of the clade H weevils mainly are borers in petioles or stems of cruciferous plants, while larvae of the clade I weevils mainly inhabit the fruits of the same plants, suggesting that ecological niche specialization can play a critical role in the diversification of Ceutorhynchus species. This study generates baseline molecular and genetic information for future research of Ceutorhynchus-related taxa and provides insights into the phylogeny and evolution of Curculionidae.

Nickel-Catalyzed α-selective Hydroalkylation of Vinylarenes.

C(sp3) centers adjacent to (hetero)aryl groups are widely present in physiologically active molecules. Metal-hydride-catalyzed hydroalkylation of alkenes represents an efficient means of forging C(sp3)-C(sp3) bonds, boasting advantages as a wide source of substrates, mild reaction conditions, and facile selectivity manipulation. Nevertheless, the hydroalkylation of vinylarenes encounters constraints in terms of substrate scope, necessitating the employment of activated alkyl halides or alkenes containing chelating groups, remains a challenge. In this context, we report a general nickel-hydride-catalyzed hydroalkylation protocol for vinylarenes. Remarkably, this system enables α-selective hydroalkylation of both aryl and heteroaryl alkenes under an extra ligand-free condition, demonstrating excellent coupling efficiency and selectivity. Furthermore, through the incorporation of chiral bisoxazoline ligands, we have achieved regio- and enantioselective hydroalkylation of vinylpyrroles, thereby facilitating the synthesis of α-branched alkylated pyrrole derivatives.

Nickel-Catalyzed Remote Asymmetric Hydroalkylation of Alkenyl Ethers to Access Ethers of Chiral Dialkyl Carbinols.

Site- and enantio-selective alkyl-alkyl bond formation is privileged in the retrosynthetic analysis due to the universality of sp3-hybridized carbon atoms in organic molecules. Herein, we report a nickel-catalyzed remote asymmetric hydroalkylation of alkenyl ethers via synchronous implementation of alkene isomerization and enantioselective C(sp3)-C(sp3) bond formation. Regression analysis of catalyst structure-activity relationships accelerates the rational ligand modification through modular regulation. This reaction has several advantages for synthesizing chiral dialkyl carbinols and their ether derivatives, including the broad substrate scope, good functional group tolerance, excellent regioselectivity (>20:1 regioisomeric ratio), and high enantioselectivity (up to 95% enantiomeric excess).

Photocatalytic Alkyl Radical Addition Tandem Oxidation of Alkenyl Borates.

Photocatalytic oxidation is a popular transformation way for organic synthesis and is widely applied in academia and industry. Herein, we report a blue light-induced alkylation-oxidation tandem reaction for the synthesis of diverse ketones by combining alkyl radical addition and oxidation of alkenyl borates. This reaction shows excellent functional group compatibility in acceptable yields, and diversity of radical precursors is applicable.

Ligand-Controlled Stereoselective Synthesis of 2-Deoxy-ß-C-glycosides by Cobalt Catalysis.

2-Deoxy-ß-C-glycosides represent an important class of carbohydrates that are present in many bioactive molecules. However, owing to the lack of substituents at the C2 position, the stereoselective synthesis of 2-deoxy-ß-C-glycosides is highly challenging. Herein, we report a ligand-controlled stereoselective C-alkyl glycosylation reaction to access 2-deoxy-ß-C-alkyl glycosides from readily available glycals and alkyl halides. This method exhibits broad substrate scope and excellent diastereoselectivity under very mild conditions. In addition, unprecedented stereodivergent synthesis of 2-deoxy-C-ribofuranosides is achieved using different chiral bisoxazoline ligands. Mechanistic studies suggest that hydrometallation of the glycal with the bisoxazoline-ligated Co-H species may be the turnover-limiting and stereodetermining step of this transformation.

Ligand-Controlled Cobalt-Catalyzed Regiodivergent Alkyne Hydroalkylation.

Regiodivergent alkyne hydroalkylation to generate different isomers of an alkene from the same alkyne starting material would be beneficial; however, it remains a challenge. Herein, we report a ligand-controlled cobalt-catalyzed regiodivergent alkyne hydroalkylation. The sensible selection of bisoxazoline (L1) and pyridine-oxazoline (L8) ligands led to reliable and predictable protocols that provided (E)-1,2-disubstituted and 1,1-disubstituted alkenes with high E/Z stereoselectivity and regioisomeric ratio starting from identical terminal alkyne and alkyl halide substrates and produced trisubstituted alkenes in the case of internal alkynes. This method exhibits a broad scope for terminal and internal alkynes with a wide range of activated and unactivated alkyl halides and shows excellent functional group compatibility.

Nucleophilicity Prediction Using Graph Neural Networks.

The quantitative description between chemical reaction rates and nucleophilicity parameters plays a crucial role in organic chemistry. In this regard, the formula proposed by Mayr et al. and the constructed reactivity database are important representatives. However, the determination of Mayr's nucleophilicity parameter N often requires time-consuming experiments with reference electrophiles in the solvent. Several machine learning (ML)-based models have been proposed to realize the data-driven prediction of N in recent years. However, in addition to DFT-calculated electronic descriptors, most of them also use a set of artificially predefined structural descriptors as input, which may result in a biased representation of the nucleophile's structural information depending on descriptors' definition preference. Compared with traditional ML algorithms, graph neural networks (GNNs) can naturally take the molecule's structural information into account by applying the message passing technique. We herein proposed a SchNet-based GNN model that only takes the molecular conformation and solvent type as input. The model achieves a comparable performance to the previous benchmark study on 10-fold cross-validation of 894 data points (R2 = 0.91, RMSE = 2.25). To enhance the model's ability to capture the molecule's electronic information, some DFT-calculated parameters are then incorporated into the model via graph global features, and substantial improvement is achieved in the prediction precision (R2 = 0.95, RMSE = 1.63). These results demonstrate that both structural and electronic information are important for the prediction of N, and GNN can integrate these two kinds of information more effectively.

Nickel-Catalyzed Switchable Site-Selective Alkene Hydroalkylation by Temperature Regulation.

Regiodivergent alkene functionalization that produces either regioisomer starting from the same raw materials is desirable. Herein, we report a nickel-catalyzed switchable site-selective alkene hydroalkylation. The selection of reaction temperatures leads to protocols that provide regiodivergent hydroalkylated products starting from a single alkene substrate. This protocol allows the convenient synthesis of α- and ß-branched protected amines, both of which are important to the fields of pharmaceutical chemistry and biochemistry. In addition, enantioenriched ß-branched alkylamines can be accessed in a catalytic asymmetric variant. Preliminary mechanistic studies indicate that the formation of a more stable nickelacycle provides the driving force of migration. The thermodynamic and kinetic properties of different reduction elimination intermediates are responsible for the switchable site-selectivity.

Transcriptome profiling revealed potentially important roles of defensive gene expression in the divergence of insect biotypes: a case study with the cereal aphid Sitobion avenae.

BACKGROUND: Many insects can develop differential biotypes on variable host plants, but the underlying molecular factors and mechanisms are not well understood. To address this issue, transcriptome profiling analyses were conducted for two biotypes of the cereal aphid, Sitobion avenae (Fabricius), on both original and alternative plants. RESULTS: Comparisons between both biotypes generated 4174 differentially expressed unigenes (DEGs). In their response to host plant shift, 39 DEGs were shared by both biotypes, whereas 126 and 861 DEGs occurred only in biotypes 1 and 3, respectively. MMC (modulated modularity clustering) analyses showed that specific DEGs of biotypes 1 and 3 clustered into five and nine transcriptional modules, respectively. Among these DEGs, defense-related genes underwent intensive expression restructuring in both biotypes. However, biotype 3 was found to have relatively lower gene transcriptional plasticity than biotype 1. Gene enrichment analyses of the abovementioned modules showed functional divergence in defensive DEGs for the two biotypes in response to host transfer. The expression plasticity for some defense related genes was showed to be directly related to fecundity of S. avenae biotypes on both original and alternative plants, suggesting that expression plasticity of key defensive genes could have significant impacts on the adaptive potential and differentiation of S. avenae biotypes on different plants. CONCLUSIONS: The divergence patterns of transcriptional plasticity in defense related genes may play important roles in the phenotypic evolution and differentiation of S. avenae biotypes. Our results can provide insights into the role of gene expression plasticity in the divergence of insect biotypes and adaptive evolution of insect populations.

Life-history responses of insects to water-deficit stress: a case study with the aphid Sitobion avenae.

BACKGROUND: Drought may become one of the greatest challenges for cereal production under future warming scenarios, and its impact on insect pest outbreaks is still controversial. To address this issue, life-history responses of the English grain aphid, Sitobion avenae (Fabricius), from three areas of different drought levels were compared under three water treatments. RESULTS: Significant differences were identified in developmental time, fecundity and adult weight among S. avenae clones from moist, semiarid and arid areas under all the three water treatments. Semiarid and arid area clones tended to have higher heritability for test life-history traits than moist area clones. We identified significant selection of water-deficit on the developmental time of 1st instar nymphs and adult weight for both semiarid and arid area clones. The impact of intermediate and severe water-stress on S. avenae's fitness was neutral and negative (e.g., decreased fecundity and weight), respectively. Compared with arid-area clones, moist- and semiarid-area clones showed higher extents of adaptation to the water-deficit level of their respective source environment. Adult weight was identified as a good indicator for S. avenae's adaptation potential under different water-stress conditions. After their exposure to intermediate water-deficit stress for only five generations, adult weight and fecundity tended to decrease for moist- and semiarid-area clones, but increase for arid-area clones. CONCLUSIONS: It is evident from our study that S. avenae clones from moist, semiarid and arid areas have diverged under different water-deficit stress, and such divergence could have a genetic basis. The impact of drought on S. avenae's fitness showed a water-level dependent pattern. Clones of S. avenae were more likely to become adapted to intermediate water-deficit stress than severe water-deficit stress. After continuous water-deficit stress of only five generations, the adaptation potential of S. avenae tended to decrease for moist and semiarid area clones, but increase for arid area clones. The rapid shift of aphids' life-history traits and adaptation potential under drought could have significant implications for their evolutionary dynamics and outbreak risks in future climate change scenarios.

Morphology and Ultrastructure of Antennal Sensilla in Male and Female Agrilus mali (Coleoptera: Buprestidae).

The apple buprestid beetle, Agrilus mali Matsumura, is an invasive pest causing significant damages to rare wild apple forests of Xinjiang. The morphology, abundance and distribution of antennal sensilla in both sexes of this pest were examined. We found that the antennae of A. mali females were longer than those of males. Five types of antennal sensilla were characterized, including trichodea (subtypes Tr.1, Tr.2, and Tr.3), chaetica (subtypes Sc.1, Sc.2, Sc.3, and Sc.4), basiconica (subtypes Ba. 1, Ba. 2, Ba. 3 and Ba.4), Böhm bristles (subtypes BB. 1, and BB. 2), and multiporous grooved sensilla. The most abundant sensilla of Ba.2 tended to occur mainly on flagellomeres 5-8 in both sexes. The last three flagellomeres tended to have the most abundant Tr.1 in both sexes. Overall, the abundance and distribution of these sensilla appeared to be highly conserved in both sexes, and their olfactory organs seemed to cluster on flagellomeres 6-8. However, some sex dimorphisms were also observed. Tr.3 and BB.2 were found only in females. Sensilla of Sc.2 were found on the pedicel and first two flagellomeres only in males. When compared with males, females showed a higher number of Sc.3, but a lower number of Sc.4 on the pedicel. These results indicate that contact cues could be important in intersexual communication in A. mali. The functional roles of these sensilla and their implications in A. mali behaviors are discussed, and further studies of identified chemosensitive sensilla can provide a foundation for developing semiochemical-based management strategies.

Impacts of Water Deficiency on Life History of Sitobion avenae Clones From Semi-arid and Moist Areas.

The climate warming trend appears to be evident with an increasing frequency of drought events in Shaanxi Province of China, which may have contributed to an increase in outbreaks of the English grain aphid, Sitobion avenae (Fabricius). To explore the potential effects of water-deficit stress on aphid outbreak risks, clones of S. avenae were collected from semi-arid and moist areas of Shaanxi. The life histories of collected clones were then compared on wheat under well-watered and moderately water-stressed conditions in the laboratory. Our results demonstrated that semi-arid area clones of S. avenae had longer developmental times, shorter reproductive times, lower fecundities, and lower net reproductive rates compared with moist area clones. Age-specific reproductive rates of moist area clones tended to be higher than those of semi-arid area clones. Significant differences between semi-arid and moist area clones were found for the survival functions when tested under water-stressed conditions, and semi-arid area clones tended to have a lower survival rate than moist area clones throughout their lives. "Population origin" (i.e., semi-arid and moist area clones) and "clone" together explained 62.74-96.56% of the total variance of tested life-history traits, suggesting the genetic basis for differentiation of clones from both areas. Significant differences in correlations, and selection differentials and gradients of life-history traits were also found between clones from both areas, providing further evidence of genetic basis for the life-history differentiation between them. Divergence between clones from both areas and its implications for S. avenae outbreaks are discussed.

The impact of climate change and the conservation of the keystone Asian honeybee using niche models and systematic prioritization.

Global warming has seriously disturbed the Earth's ecosystems, and in this context, Asian honeybee (Apis cerana) has experienced a dramatic decline in recent decades. Here, we examined both direct and indirect effects of climate change on A. cerana through ecological niche modeling of A. cerana, and its disease pathogens (i.e., Chinese sacbrood virus and Melissococcus plutonius) and enemies (i.e., Galleria mellonella and Vespa mandarinia). Ecological niche modeling predicts that climate change will increase the potential suitability of A. cerana, but it will also cause some of the original habitat areas to become unsuitable. Outbreak risks of Chinese sacbrood disease and European Foulbrood will increase dramatically, while those of G. mellonella and V. mandarinia will decrease only slightly. Thus, climate change will produce an unfavorable situation for even maintaining some A. cerana populations in China in the future. Genetic structure analyses showed that the A. cerana population from Hainan Island had significant genetic differentiation from that of the mainland, and there was almost no gene flow between the 2, suggesting that urgent measures are needed to protect the unique genetic resources there. Through taking an integrated planning technique with the Marxan approach, we optimized conservation planning, and identified potential nature reserves (mainly in western Sichuan and southern Tibet) for conservation of A. cerana populations. Our results can provide insights into the potential impact of climate change on A. cerana, and will help to promote the conservation of the keystone honeybee in China and the long-term sustainability of its ecosystem services.

Differential performance of Sitobion avenae (Hemiptera: Aphididae) clones from wheat and barley with implications for its management through alternative cultural practices.

Cultural control measures should play an important role in cereal aphid management on wheat and barley. Planting barley in fields adjacent to those of wheat and intercropping wheat with barley are cultural practices that might suppress the cosmopolitan cereal pest Sitobion avenae (F.). To evaluate the potential effects of these cultural measures on aphid outbreak risks, clones of S. avenae were collected from wheat and barley. Host-switch experiments for the collected clones were conducted in the laboratory to compare their life table parameters and other life history traits. Our results demonstrated that wheat clones of S. avenae had lower developmental times, higher fecundities, and higher growth rates compared with barley clones when tested on the plant of origin. When transferred to barley, the performance of wheat clones was decreased in terms of developmental times of nymphs and age at first reproduction of adults. Barley clones' performance was decreased in terms of reproductive time or lifespan of adult on wheat compared with that on barley. The age-specific survival rates of barley clones tended to be lower than wheat clones in the earlier part of their lives on wheat. The age-specific fecundity of barley clones on barley remained low and fluctuated significantly during their lifetime. Although quite a few significant correlations between developmental and reproductive traits were identified on both plants, no significantly negative correlations (i.e., trade-offs) for the traits were found between plants. The results suggested that barley clones could be generalized but wheat clones were more specialized to their host plant. The potential benefits of the abovementioned cultural measures were discussed.

Rapid Changes in Composition and Contents of Cuticular Hydrocarbons in Sitobion avenae (Hemiptera: Aphididae) Clones Adapting to Desiccation Stress.

Cuticular hydrocarbons (CHCs) are diverse in insects, and include variable classes of cuticular lipids, contributing to waterproofing for insects under desiccation environments. However, this waterproofing function of CHCs is still not well characterized in aphids. In this study, we compared CHC profiles for desiccation-resistant and nonresistant genotypes of the grain aphid, Sitobion avenae (Fabricius), in responses to desiccation. Our result showed that a total of 27 CHCs were detected in S. avenae, and linear alkanes (e.g., n-C29) were found to be the predominant components. Long-chain monomethyl alkanes were found to associate closely with water loss rates in S. avenae in most cases. Resistant genotypes of both wing morphs had higher contents of short-chain n-alkanes under control than nonresistant genotypes, showing the importance of short-chain n-alkanes in constitutive desiccation resistance. Among these, n-C25 might provide a CHC signature to distinguish between desiccation-resistant and nonresistant individuals. Compared with linear alkanes, methyl-branched CHCs appeared to display higher plasticity in rapid responses to desiccation, especially for 2-MeC26, implying that methyl-branched CHCs could be more sensitive to desiccation, and play more important roles in induced desiccation-resistance. Thus, both constitutive and induced CHCs (linear or methyl-branched) can contribute to adaptive responses of S. avenae populations under desiccation environments. Our results provide substantial evidence for adaptive changes of desiccation resistance and associated CHCs in S. avenae, and have significant implications for aphid evolution and management in the context of global climate change.

Structure and distribution of antennal sensilla in Pseudosymmachia flavescens (Brenske) (Coleoptera: Scarabaeidae: Melolonthinae).

Morphology, microstructure, and distribution of antennal sensilla were compared between female and male Pseudosymmachia flavescens (Brenske) (Coleoptera: Scarabaeidae: Melolonthinae). Lamellate antennae of P. flavescens were shown to have typical scape, pedicel, and flagellum segments. The flagellum consists of a four-segmented funicle and a three-segmented club. The lengths of their pedicel and funicle were found to be similar in females and males. Distinct sexual differences were observed in the length of lamellar segments. Nine types/subtypes of sensilla were identified on the antennae of both sexes, including Böhm sensilla, sensilla trichodea, sensilla basiconica (SB), and two subtypes for sensilla chaetica, sensilla coeloconica, and sensilla placodea each. Olfactory sensilla (e.g., SB and placodea) are mainly located on three lamellar segments of the antennal club. Variation was also seen in abundance of various types of antennal sensilla, with males possessing significantly more sensilla than females. Sensilla placodea were the most abundant, and their number in males was twice of that in females, showing a clear sexual dimorphism. The difference in the distribution of sensilla placodea might reflect their roles in sexual chemical communication.

Increasing risk of aphids spreading plant viruses in maize fields on both sides of China's Heihe-Tengchong line under climate change.

BACKGROUND: In the coming decades, geographical distribution patterns of farmland organisms may undergo drastic changes due to climate change, with significant implications for global food security. In China, Rhopalosiphum maidis and its spread of sugarcane mosaic virus (ScMV) can become an increasingly serious threat to maize (Zea mays) production. We conducted ecological niche modeling for Z. mays, R. maidis, and ScMV under current and future (2041-2060 and 2081-2100) climate scenarios by using MaxEnt software to explore changes in this system. RESULTS: The Heihe-Tengchong line (an imaginary separation line of human population density) can divide China into main (east of the line) and secondary (west of the line) habitats for the three species. With climate change, rapid expansion in suitable areas is projected for ScMV and the aphid vector R. maidis. Taking species interactions into consideration, our overlaying analyses show that most areas east of the Heihe-Tengchong line (optimal for maize and suitable for R. maidis) will become increasingly highly suitable for ScMV, suggesting that the prevention and control of this plant virus and its aphid vector in China's main maize-growing areas (e.g. northeast) will become an increasing challenge in the future. CONCLUSION: Climate change will profoundly affect ScMV-vector-maize interactions, which may contribute favorably to invasion of this virus into new areas. Our comprehensive and in-depth analyses on shifts in this multi-species system under climate change provide useful and insightful information for devising strategies for the prevention and control of plant viruses and aphid vectors on maize in the future. © 2022 Society of Chemical Industry.

Functional Characterization of Chemosensory Protein AmalCSP5 From Apple Buprestid Beetle, Agrilus mali (Coleoptera: Buprestidae).

In the sensitive and complex chemo-sensation system of insects, chemosensory proteins (CSPs) can facilitate the transfer of chemical information and play important roles for variable behaviors of insects. We cloned the chemosensory protein AmalCSP5 from antennae of the apple buprestid beetle (Agrilus mali Matsumura), a serious invasive pest of wild apple trees. Expression profiling showed that AmalCSP5 was expressed in various tissues, suggesting its significance in multiple physiological activities and behaviors of A. mali. AmalCSP5 was preferentially expressed in female antennae and male abdomens. AmalCSP5 was able to bind a variety of test volatiles, especially alcohols and esters. AmalCSP5 exhibited good binding affinity for all five test secondary compounds (i.e., procyanidin, phlorizin, kaemferol, chlorogenic acid, and rutin), suggesting its preferential binding abilities to nonvolatile host plant secondary metabolites and critical roles in gustatory perception of nonvolatiles. Tyr27 and Ser69 of AmalCSP5 could form hydrogen bonds with hexyl benzoate and hexyl hexanoate, respectively. Procyanidin, the best ligand among all test compounds, could form hydrogen bonds with three amino acid residues (i.e., Arg7, Leu8, and Lys41) of AmalCSP5. Thus, high ligand binding affinity for AmalCSP5 seemed to be dependent mainly on the formation of hydrogen bonds. The putative key amino acid residues of AmalCSP5 can be used as molecular targets for designing and screening new attractants and repellents for A. mali. Our results provide insights into binding interactions of AmalCSP5 with volatile and nonvolatile ligands, and a firm basis for developing eco-friendly management strategies of A. mali.

Analyses of structural dynamics revealed flexible binding mechanism for the Agrilus mali odorant binding protein 8 towards plant volatiles.

BACKGROUND: Volatiles from host plants are an important source of insect pest attractants and repellents. Insect odorant binding proteins (OBPs) have been widely characterized, but the molecular binding dynamics and underlying mechanisms are still not well understood. Thus, we characterized binding characteristics of AmalOBP8 from the apple buprestid beetle (Agrilus mali Matsumura), an unprecedented serious threat to rare apple germplasm resources and local ecosystems. RESULTS: Fluorescence studies demonstrated that the quenching mechanism was clearly static. AmalOBP8 was found to bind with both volatiles at single independent sites. Negative thermodynamic parameters suggested that binding interactions between AmalOBP8 and both volatiles could occur spontaneously. Hydrogen bonding was the key force in AmalOBP8's binding to geranyl formate, for which the amino acid residue Trp106 played a critical role in the binding pocket. Multiple Leu residues in AmalOBP8 created a strong hydrophobic environment, and formed the binding pocket for (Z)-3-hexenyl hexanoate. Compared to classic OBPs, in addition to lack of one disulfide bridge, AmalOBP8 had a small α-helix (α7) at the C-terminus, resulting in greater flexibility and adaptability for this protein to bind with different compound molecules. CONCLUSION: Key residues of AmalOBP8 in binding interactions with plant volatiles were clarified. AmalOPB8 had a large ligand binding spectrum and great flexibility in binding with plant volatiles, providing good molecular targets for screening insect attractants and repellents. Our results can promote understanding of insects' perception of various odorants, and establish a foundation for discovery of new pest control agents. © 2020 Society of Chemical Industry.

Transition-metal-free decarboxylative thiolation of stable aliphatic carboxylates.

A transition-metal-free decarboxylative thiolation protocol is reported in which primary, secondary, tertiary (hetero)aryl acetates and α-CN substituted acetates undergo the decarboxylative thiolation smoothly, to deliver a variety of functionalized aryl alkyl sulfides in moderate to excellent yields. Aryl diselenides are also amenable substrates for construction of C-Se bonds under the simple and mild reaction conditions. Moreover, the protocol is successfully applied to the late-stage modification of pharmaceutical carboxylates with satisfactory chemoselectivity and functional-group compatibility.