Asymmetric Three-Component Radical Alkene Carboazidation by Direct Activation of Aliphatic C–H Bonds

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(19), С. 13347 - 13355

Опубликована: Май 6, 2024

Azide compounds are widely present in natural products and drug molecules, their easy-to-transform characteristics make them used the field of organic synthesis. The merging transition-metal catalysis with radical chemistry offers a versatile platform for carboazidation alkenes, allowing rapid assembly highly functionalized azides. However, direct use readily available hydrocarbon feedstocks as sp

Язык: Английский

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Unleashing the potentiality of metals: synergistic catalysis with light and electricity

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(14), С. 4024 - 4040

Опубликована: Янв. 1, 2024

This review provides a comprehensive overview of metal catalysis in photo-electrochemical systems, discussing reaction mechanisms and offering prospects for this triadic catalytic mode.

Язык: Английский

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Cu-Catalyzed Relay Functionalization of Alkenes: Diverse Synthesis of Diazidated Quinazolinones and Polycyclic Imidazoles

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 9, 2025

A Cu-catalyzed relay process for the preparation of diazidated quinazolinone and polycyclic imidazole derivatives in which readily available alkene-tethered substrates undergo an addition/cyclization/C(sp3)–H functionalization alkene sequences with high efficiency is described. Various functionalized N-heteropolycyclic compounds were prepared good yields a broad substrate scope. Moreover, direct azidation α-C(sp3)–H bond corresponding N-heterocycles has been demonstrated on basis mechanistic studies, provide alternative late-stage approach derivatization N-heterocyclic scaffolds.

Язык: Английский

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A Metal-Free Oxidative Azidation Method for Selective Azidation of C(sp³)–H Bonds and Diazidation of Alkenes

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 21, 2025

Current metal-free methods for the synthesis of alkyl (1,2-di)azides mainly rely on highly reactive hypervalent iodine reagents and electrochemical methods, which require specialized devices. Herein, we show a robust Selectfluor-promoted oxidative azidation method, can effectively achieve selective C(sp3)-H bonds in alkanes/methylarenes diazidation alkenes, without involving any metal catalyst additive. The utility this method is highlighted by broad substrate scope, late-stage functionalization, gram-scale synthesis. Mechanistic studies indicate that reaction proceeds via radical process.

Язык: Английский

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Iron-Catalyzed Three-Component Asymmetric Carboazidation of Alkenes with Alkanes and Trimethylsilyl Azide

Synlett, Год журнала: 2024, Номер unknown

Опубликована: Июнь 25, 2024

Abstract The fusion of transition-metal catalysis with radical chemistry provides a versatile platform for the asymmetric carboazidation alkenes to enable rapid assembly highly functionalized chiral azide compounds. Here, we present an iron-catalyzed three-component that processes electron-deficient by direct activation aliphatic C–H bonds. This strategy access range valuable azides from readily available chemical feedstocks bearing tetrasubstituted carbon stereocenter, and their synthetic potential is further showcased through straightforward transformations provide other enantioenriched building blocks.

Язык: Английский

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Building Catalytic Reactions One Electron at a Time

Accounts of Chemical Research, Год журнала: 2024, Номер unknown

Опубликована: Сен. 24, 2024

ConspectusClassical education in organic chemistry and catalysis, not the least my own, has centered on two-electron transformations, from nucleophilic attack to oxidative addition. The focus is well-founded, as this brand of enabled incredible feats synthesis, development life-saving pharmaceuticals production ubiquitous commodity chemicals. With that said, approach many ways complementary nature, where enzymes frequently make use single-electron "radical" steps achieve challenging reactions with exceptional selectivity, including light detection C-H hydroxylation. While power radical elementary undeniable, fundamental understanding of─and ability apply─these catalysis remains underdeveloped, constraining palette which chemists can new reactions.Motivation remedy traditional underemphasis been intensified by runaway success outer-sphere photoredox only confirming versatility radicals anthropogenic but also teaching value robust well-understood catalytic cycles for reaction design. Indeed, I would argue fueled strong its underlying steps, consideration transfer (SET) energetics allowing be designed

Язык: Английский

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Direct Selective Azidation of C(sp3)−H Groups

Tetrahedron Chem, Год журнала: 2024, Номер unknown, С. 100114 - 100114

Опубликована: Ноя. 1, 2024

Язык: Английский

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