Photoredox/Nickel-Catalyzed Single-Electron Tsuji-Trost Reaction: Development and Mechanistic Insights

被引：79

作者：

Matsui, Jennifer K. ^{[1
]}

Gutierrez-Bonet, Alvaro ^{[1
]}

Rotella, Madeline ^{[2
]}

Alam, Rauful ^{[1
]}

Gutierrez, Osvaldo ^{[2
]}

Molander, Gary A. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

[2] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 48期

基金：

美国国家科学基金会;

关键词：

allylic compounds; nickel; photochemistry; reaction mechanism; synthetic methods; HANTZSCH 1,4-DIHYDROPYRIDINES; SUBSTITUTION-REACTIONS; ALLYLIC ALKYLATION; ACYL CHLORIDES; DUAL CATALYSIS; NICKEL; ALLYLATION; TRANSMETALATION; HALIDES; ESTERS;

D O I：

10.1002/anie.201809919

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A regioselective, nickel-catalyzed photoredox allylation of secondary, benzyl, and alpha-alkoxy radical precursors is disclosed. Through this manifold, a variety of linear allylic alcohols and allylated monosaccharides are accessible in high yields under mild reaction conditions. Quantum mechanical calculations [DET and DLPNO-CCSD(T)/support the mechanistic hypothesis of a Ni-0 to Ni-11 oxidative addition pathway followed by radical addition and inner-sphere allylation.

引用

页码：15847 / 15851

页数：5

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