Visible-Light Photocatalytic Barbier-Type Reaction of Aziridines and Azetidines with Nonactivated Aldehydes

被引：2
|
作者：
Qu, Quan [1 ]
Chen, Lin [2 ]
Deng, Yu [2 ]
Gui, Yong-Yuan [1 ]
Yu, Da-Gang [2 ,3 ]
机构：
[1] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610068, Peoples R China
[2] Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, 29 Wangjiang Rd, Chengdu 610064, Peoples R China
[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
SYNLETT | 2023年 / 34卷 / 12期
基金：
中国国家自然科学基金;
关键词：
photocatalysis; Barbier reaction; aziridines; azetidines; C-N bond cleavage; CATALYZED SELECTIVE CARBOXYLATION; NONRACEMIC 1,3-AMINO ALCOHOLS; BOND-FORMING REACTIONS; RING-OPENING REACTIONS; BETA-AMINO ALCOHOLS; STEREOSELECTIVE-SYNTHESIS; EN-ROUTE; KETONES; ALLYLATION; CHEMISTRY;
D O I：
10.1055/a-2039-9942
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Barbier-type reactions are a classic group of reactions for carbon-carbon bond formation; however, their common use of stoichiometric metals restricts their widespread application. Considering the ready availability and diversity of cyclic amines, we report a visible-light photocatalytic Barbier-type reaction of aziridines and azetidines with nonactivated aldehydes. A series of important gamma-and delta-amino alcohols were synthesized in the presence of amines as electron donors. Moreover, this transition-metal-free protocol displays mild reaction conditions, broad functional-group tolerance, and a wide substrate scope. Mechanistic investigations indicated that carbon radicals and carbanions might be generated as key intermediates.
引用
收藏
页码：1385 / 1390
页数：6
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