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1.
Angew Chem Int Ed Engl ; 62(8): e202217386, 2023 Feb 13.
Artigo em Inglês | MEDLINE | ID: mdl-36576703

RESUMO

Herein, we describe the development of a copper-catalyzed C(sp3 )-amination of proaromatic dihydroquinazolinones derived from ketones. The reaction is enabled by the intermediacy of open-shell species arising from homolytic C-C bond-cleavage driven by aromatization. The protocol is characterized by its operational simplicity and generality, including chemical diversification of advanced intermediates.

2.
J Am Chem Soc ; 142(49): 20594-20599, 2020 12 09.
Artigo em Inglês | MEDLINE | ID: mdl-33252234

RESUMO

A dual platform for forging sp2-sp3 and sp3-sp3 carbon bonds via catalytic ß-scission of aliphatic alcohol derivatives with both aryl and alkyl halides is disclosed. This protocol is distinguished by its wide substrate scope and broad applicability, even in the context of late-stage functionalization.

3.
J Am Chem Soc ; 141(7): 2889-2893, 2019 02 20.
Artigo em Inglês | MEDLINE | ID: mdl-30735367

RESUMO

A functional group exchange reaction between allylamines and alkenes via nickel-catalyzed C-C bond cleavage and formation was developed. This reaction provides a novel protocol, which does not require the use of unstable imine substrates, for the synthesis of allylamines, which are widely used in the production of fine chemicals, pharmaceuticals, and agrochemicals.

4.
Org Lett ; 25(20): 3750-3754, 2023 May 26.
Artigo em Inglês | MEDLINE | ID: mdl-37195763

RESUMO

Herein, we describe the development of a copper-catalyzed C(sp3) amination of unactivated secondary alkyl iodides mediated by diaryliodonium salts. Our protocol is enabled by the intermediacy of aryl radical species that undergo halogen atom transfer prior to interfacing with copper catalysts, thus setting the basis for a C-N bond formation at sp3-hybridized carbons. The method is characterized by its mild reaction conditions, excellent regioselectivity, and wide substrate scope.

5.
Front Microbiol ; 14: 1257442, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-38152372

RESUMO

Phosphorus (P) deficiency is a predominant constraint on plant growth in acidified soils, largely due to the sequestration of P by toxic aluminum (Al) compounds. Indigenous phosphorus-solubilizing bacteria (PSBs) capable of mobilizing Al-P in these soils hold significant promise. A novel Al-P-solubilizing strain, Al-P Nguyenibacter sp. L1, was isolated from the rhizosphere soil of healthy Lespedeza bicolor plants indigenous to acidic terrains. However, our understanding of the genomic landscape of bacterial species within the genus Nguyenibacter remains in its infancy. To further explore its biotechnological potentialities, we sequenced the complete genome of this strain, employing an amalgamation of Oxford Nanopore ONT and Illumina sequencing platforms. The resultant genomic sequence of Nguyenibacter sp. L1 manifests as a singular, circular chromosome encompassing 4,294,433 nucleotides and displaying a GC content of 66.73%. The genome was found to host 3,820 protein-coding sequences, 12 rRNAs, and 55 tRNAs. Intriguingly, annotations derived from the eggNOG and KEGG databases indicate the presence of genes affiliated with phosphorus solubilization and nitrogen fixation, including iscU, glnA, and gltB/D associated with nitrogen fixation, and pqqBC associated with inorganic phosphate dissolution. Several bioactive secondary metabolite genes in the genome, including pqqCDE, phytoene synthase and squalene synthase predicted by antiSMASH. Moreover, we uncovered a complete metabolic pathway for ammonia, suggesting an ammonia-affinity property inherent to Nguyenibacter sp. L1. This study verifies the nitrogen-fixing and phosphate-dissolving abilities of Nguyenibacter sp. L1 at the molecular level through genetic screening and analysis. The insights gleaned from this study offer strategic guidance for future strain enhancement and establish a strong foundation for the potential incorporation of this bacterium into agricultural practices.

6.
Nat Commun ; 13(1): 2394, 2022 05 03.
Artigo em Inglês | MEDLINE | ID: mdl-35504911

RESUMO

C-C bond forming cross-couplings are convenient technologies for the construction of functional molecules. Consequently, there is continual interest in approaches that can render traditionally inert functionality as cross-coupling partners, included in this are ketones which are widely-available commodity chemicals and easy to install synthetic handles. Herein, we describe a dual catalytic strategy that utilizes dihydroquinazolinones derived from ketone congeners as adaptative one-electron handles for forging C(sp3) architectures via α C-C cleavage with aryl and alkyl bromides. Our approach is achieved by combining the flexibility and modularity of nickel catalysis with the propensity of photoredox events for generating open-shell reaction intermediates. This method is distinguished by its wide scope and broad application profile--including chemical diversification of advanced intermediates--, providing a catalytic technique complementary to existing C(sp3) cross-coupling reactions that operates within the C-C bond-functionalization arena.


Assuntos
Níquel , Processos Fotoquímicos , Alquilação , Catálise , Cetonas , Níquel/química , Oxirredução
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