Divergent regioselectivity in photoredox-catalyzed hydrofunctionalization reactions of unsaturated amides and thioamides

被引：102

作者：

Morse, Peter D. ^{[1
]}

Nicewicz, David A. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

CHEMICAL SCIENCE | 2015年 / 6卷 / 01期

关键词：

ANTI-MARKOVNIKOV HYDROAMINATION; ALLYLIC AMIDES; ALKENES; ACIDS; 2-THIAZOLINES; 2-OXAZOLINES; CYCLIZATION; INHIBITORS; OXAZOLES; SYSTEM;

D O I：

10.1039/c4sc02331e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A direct method to construct 2-oxazolines and 2-thiazolines from corresponding allylic amides and thioamides is reported. The redox-neutral intramolecular hydrofunctionalization is enabled by a dual catalyst system comprised of 9-mesityl-N-methyl acridinium tetrafluoroborate and phenyl disulphide and exhibits complete selectivity for the anti-Markovnikov regioisomeric products. The cyclization of allylic thioamides is postulated to operate via a modified mechanism in which oxidation of the thioamide, rather than the alkene, is responsible for the observed reactivity.

引用

页码：270 / 274

页数：5

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