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
收藏
页码：15847 / 15851
页数：5
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