Electro-/photocatalytic alkene-derived radical cation chemistry: recent advances in synthetic applications

Chemical Society Reviews, Год журнала: 2022, Номер 51(16), С. 7206 - 7237

Опубликована: Янв. 1, 2022

This review covers the recent progress in electro-/photo-catalytic alkene-derived radical cation chemistry for organic synthesis, including synthetic strategies, plausible mechanisms and further research outlook.

Язык: Английский

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Atomically Dispersed Co-N/C Catalyst for Divergent Synthesis of Nitrogen-Containing Compounds from Alkenes

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(7), С. 4142 - 4149

Опубликована: Фев. 8, 2023

Alkene functionalization with a single-atom catalyst (SAC) which merges homogeneous and heterogeneous catalysis is fascinating route to obtain high-value-added molecules. However, C–N bond formation of alkene SAC still unexplored. Herein, bimetal-organic framework-derived Co–N/C an atomically dispersed cobalt center reported show good activity chemoselective aziridination/oxyamination reactions from hydroxylamine, late-stage complex alkenes diversified synthetic transformations the aziridine product further expand utility this method. Moreover, system proceeds without external oxidants exhibits mild, atom-economic, recyclable characters. Detailed spectroscopic characterizations mechanistic studies revealed structure catalytic possible intermediates involved in mechanism cycle.

Язык: Английский

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Silver‐Enabled General Radical Difluoromethylation Reaction with TMSCF₂H

Angewandte Chemie International Edition, Год журнала: 2020, Номер 60(8), С. 4300 - 4306

Опубликована: Ноя. 16, 2020

Abstract A silver‐mediated oxidative difluoromethylation of styrenes and vinyl trifluoroborates with TMSCF 2 H is reported for the first time. This method enables direct facile access to CF H‐alkenes from abundant alkenes excellent functional‐group compatibility. Moreover, this Ag/TMSCF protocol could further enable a series radical reactions wide array substrates, offering generic complementary platform construction diversified C−CF bonds.

Язык: Английский

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Three-component 1,2-dicarbofunctionalization of alkenes involving alkyl radicals

Chemical Communications, Год журнала: 2021, Номер 58(6), С. 730 - 746

Опубликована: Дек. 8, 2021

This article provides a comprehensive perspective on three-component 1,2-dicarbofunctionalization of alkenes involving alkyl radicals, which generated from structurally diverse electrophilic and nucleophilic precursors under mild conditions.

Язык: Английский

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Recent advances in acyl radical enabled reactions between aldehydes and alkenes

Chemical Communications, Год журнала: 2021, Номер 57(50), С. 6111 - 6120

Опубликована: Янв. 1, 2021

Acyl radical enabled reactions between aldehydes and alkenes.

Язык: Английский

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Intermolecular 1,2-Difunctionalization of Alkenes Enabled by Fluoroamide-Directed Remote Benzyl C(sp³)–H Functionalization

Journal of the American Chemical Society, Год журнала: 2021, Номер 144(1), С. 339 - 348

Опубликована: Дек. 22, 2021

A copper-catalyzed remote benzylic C-H functionalization strategy enabling 1,2-difunctionalization of alkenes with 2-methylbenzeneamides and nucleophiles, including alcohols, indoles, pyrroles, the intrinsic amino groups, is reported, which characterized by its redox-neutral conditions, exquisite site-selectivity, broad substrate scope, wide utilizations late-stage modifying bioactive molecules. This reaction proceeds through nitrogen-centered radical generation, hydrogen atom transfer, addition across alkenes, single-electron oxidation, carbocation electrophilic course cascades. While using external nucleophiles manipulates three-component alkene alkylalkoxylation alkyl-heteroarylation to access dialkyl ethers, 3-alkylindoles, 3-alkylpyrroles, omitting results in two-component alkylamidation ([5+2] annulation) benzo-[f][1,2]thiazepine 1,1-dioxides.

Язык: Английский

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Synthesis of β-hydroxysulfides via visible-light-driven and EDA complex-promoted hydroxysulfenylation of styrenes with heterocyclic thiols in EtOH under photocatalyst-free conditions

Green Chemistry, Год журнала: 2022, Номер 24(8), С. 3250 - 3256

Опубликована: Янв. 1, 2022

A convenient, environmentally friendly, visible-light-driven and EDA complex-promoted direct hydroxysulfenylation of styrenes under photocatalyst- transition metal-free has been developed with O 2 as the oxygen source EtOH solvent.

Язык: Английский

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Highly Selective Radical Relay 1,4-Oxyimination of Two Electronically Differentiated Olefins

Journal of the American Chemical Society, Год журнала: 2022, Номер 144(47), С. 21664 - 21673

Опубликована: Ноя. 16, 2022

Radical addition reactions of olefins have emerged as an attractive tool for the rapid assembly complex structures, and plentiful applications in organic synthesis, however, such are often limited to polymerization or 1,2-difunctionalization. Herein, we disclose unprecedented radical relay 1,4-oxyimination two electronically differentiated with a class bifunctional oxime carbonate reagents via energy transfer strategy. The protocol is highly chemo- regioselective, three different chemical bonds (C-O, C-C, C-N bonds) were formed single operation orchestrated manner. Notably, this reaction provides access large variety structurally diverse products, obtained products could be easily converted into valuable biologically relevant δ-hydroxyl-α-amino acids. With combination experimental theoretical methods, mechanism has been investigated. Theoretical calculations reveal that chain might operate reaction.

Язык: Английский

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Transition-metal-free three-component acetalation-pyridylation of alkenes via photoredox catalysis

CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION), Год журнала: 2022, Номер 43(3), С. 571 - 583

Опубликована: Фев. 2, 2022

Язык: Английский

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Electrophotocatalytic Reductive 1,2‐Diarylationof Alkenes with Aryl Halides and Cyanoaromatics

Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(16), С. 1921 - 1930

Опубликована: Апрель 7, 2023

Comprehensive Summary The radical‐mediated reductive functionalization of aryl halides has been extensively studied. However, the related intermolecular 1,2‐diarylation alkenes, using as radical sources, remains unexplored. Herein, a new electrophotocatalytic alkenes is reported and cyanoaromatics to produce polyarylated alkanes. Using synergistic cathodic reduction visible‐light photoredox catalysis, various electron‐rich electron‐deficient are combined with characterize broad substrate scope, excellent functional group compatibility, selectivity this reaction. Mechanistic investigations reveal that reaction may proceed via process initiated by generation radicals from terminated radical‐radical coupling cyanoaromatic anions.

Язык: Английский

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