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1.
Chem Soc Rev ; 53(5): 2326-2349, 2024 Mar 04.
Artículo en Inglés | MEDLINE | ID: mdl-38259195

RESUMEN

As a class of multifunctional reagents, organic peroxides play vital roles in the chemical industry, pharmaceutical synthesis and polymerization reactions. Metal-catalyzed asymmetric catalysis has emerged as one of the most straightforward and efficient strategies to construct enantioenriched molecules, and an increasing number of metal-catalyzed asymmetric reactions enabled by organic peroxides have been disclosed by researchers in recent years. Despite remarkable progress, the types of asymmetric reactions facilitated by organic peroxides remain limited and the catalysis systems need to be further broadened. To the best of our knowledge, there is still no review devoted to summarizing the reactions from this perspective. In this review, we will endeavor to highlight the advances in metal-catalyzed asymmetric reactions enabled by organic peroxides. We hope that this survey will summarize the functions of organic peroxides in catalytic reactions, improve the understanding of these compounds and inspire future developments in this area.

2.
Org Lett ; 22(3): 991-996, 2020 02 07.
Artículo en Inglés | MEDLINE | ID: mdl-31967845

RESUMEN

α-Deuterated alcohols have important applications in pharmaceuticals and mechanism studies. Here, we report a new and practical strategy for the reductive deuteration of ketones using a Mg/BrCH2CH2Br/D2O system, which affords α-deuterated alcohols in good yields and with almost quantitative incorporation of deuterium. The synthetic value of this method has been demonstrated by the easy access to deuterated drugs or drug derivatives. This method may inspire the discovery of other deuterium-containing drugs.

3.
iScience ; 23(4): 101031, 2020 Apr 24.
Artículo en Inglés | MEDLINE | ID: mdl-32299054

RESUMEN

Carbon-carbon bond formation through polarity reversal ketyl radical anion coupling of carbonyls has inspired new reaction modes to this cornerstone carbonyl group and played significant roles in organic chemistry. The introduction of this resplendent polarity reversal ketyl strategy into polymer chemistry will inspire new polymerization mode with unpredicted discoveries. Here we show the successful introduction of polarity reversal ketyl approach to polymer chemistry to realize self-condensing ketyl polymerization with polymerization-induced emission. In this polarity reversal approach, it exhibits intriguing reversed polymerizability, where traditional excellent leaving groups are not suitable for polymerization but challenging polymerizations involving the cleavage of challenging C-F and C-CF3 bonds are realized under mild Barbier conditions. This polarity reversal approach enables the polymer chemistry with polarity reversal ketyl mode, opens up a new avenue toward the polymerization of challenging C-X bonds under mild conditions, and sparks design inspiration of new reaction, polymerization, and functional polymer.

4.
iScience ; 23(3): 100902, 2020 Mar 27.
Artículo en Inglés | MEDLINE | ID: mdl-32106054

RESUMEN

Polymerization and modification play central roles in polymer chemistry and are generally implemented in two steps, which suffer from the time-consuming two-step strategy and present considerable challenge for complete modification. By introducing the radical cascade reaction (RCR) into polymer chemistry, a one-step strategy is demonstrated to achieve synchronized polymerization and complete modification in situ. Attributed to the cascade feature of iron-catalyzed three-component alkene carboazidation RCR exhibiting carbon-carbon bond formation and carbon-azide bond formation with extremely high efficiency and selectivity in one step, radical cascade polymerization therefore enables the in situ synchronized polymerization through continuous carbon-carbon bond formation and complete modification through carbon-azide bond formation simultaneously. This results in a series of α, ß, and γ poly(amino acid) precursors. This result not only expands the methodology library of polymerization, but also the possibility for polymer science to achieve functional polymers with tailored chemical functionality from in situ polymerization.

5.
Org Lett ; 19(1): 46-49, 2017 01 06.
Artículo en Inglés | MEDLINE | ID: mdl-27936779

RESUMEN

An efficient, iron-catalyzed C-H alkylation of benzothiazoles by using alkyl diacyl peroxides and alkyl tert-butyl peresters which are readily accessible from carboxylic acids to synthesize 2-alkylbenzothiazoles is developed. This reaction is environmentally benign and compatible with a broad range of functional groups. Various primary, secondary, and tertiary alkyl groups can be efficiently incorporated into diverse benzothiazoles. The effectiveness of this method is illustrated by late-stage functionalization of biologically active heterocycles.

6.
Chem Sci ; 8(3): 2081-2085, 2017 Mar 01.
Artículo en Inglés | MEDLINE | ID: mdl-28451327

RESUMEN

Short alkyl chain Heck (type) reactions, especially methyl Heck reactions, are a difficult aspect of the alkyl Heck reaction. To provide a solution to this problem, iron-catalyzed methyl, ethyl and propyl Heck reactions were developed using readily available alkyl peroxides as alkyl sources. The reaction conditions were mild, clean, and easy to handle. No additive was needed, and no hazardous waste was generated. The products were obtained in up to 99% yield of one isomer for most situations. This reaction works for many types of olefin and tolerates a variety of functional groups. Several late-stage functionalizations of natural products and drug molecules were conducted to demonstrate the synthetic applications of this reaction.

7.
Org Lett ; 19(18): 4718-4721, 2017 09 15.
Artículo en Inglés | MEDLINE | ID: mdl-28862865

RESUMEN

γ-Amino butyric acid (GABA) is the chief inhibitory neurotransmitter in the mammalian central nervous system. Many GABA derivatives are used clinically to prevent or treat neurodegenerative diseases. Copper-catalyzed carboamination of alkenes offers an efficient method to fashion the core structure of GABA derivatives from alkenes. In this reaction, acetonitrile serves as the source of the carbon and nitrogen functionalities used to difunctionalize alkenes. Experimental and density functional theory (DFT) studies were carried out to investigate the mechanism of the reaction, and a copper-catalyzed radical-polar crossover mechanism is proposed.

8.
Org Lett ; 18(3): 392-5, 2016 Feb 05.
Artículo en Inglés | MEDLINE | ID: mdl-26790009

RESUMEN

Copper catalyzed 1,2-alkylesterification of 1,3-dienes with diacyl peroxides affords branched allylic esters in excellent regioselectivity, including products with a newly generated fully substituted carbon center. The only byproduct is CO2. The reaction proceeds by a radical mechanism as suggested by spin trap and crossover experiments.

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