Catalytic Direct Cyclization of Alkenyl Thioester

被引：43

作者：

Date, Shiori ^{[1
]}

Hamasaki, Kensei ^{[1
]}

Sunagawa, Karen ^{[1
]}

Koyama, Hiroki ^{[1
]}

Sebe, Chikayoshi ^{[1
]}

Hiroya, Kou ^{[1
]}

Shigehisa, Hiroki ^{[1
]}

机构：

[1] Musashino Univ, Nishitokyo, Japan

来源：

ACS CATALYSIS | 2020年 / 10卷 / 03期

关键词：

hydrogen atom transfer; radical polar crossover; hydrothiolation; thioester; alkene; COBALT-CARBON BONDS; COMPLEXES; HYDROFUNCTIONALIZATION; TETRAHYDROTHIOPHENES; HYDROAMINATION; HYDROGENATION; CLEAVAGE; OLEFINS; MN; FE;

D O I：

10.1021/acscatal.9b05045

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Herein we report a one-step, catalytic, Markovnikov-selective, and scalable method for the synthesis of saturated sulfur heterocycles, which are found in the structures of pharmaceuticals and natural products, from an alkenyl thioester. Unlike a potentially labile alkenyl thiol, an alkenyl thioester is stable and easy to prepare. Powerful catalysis via a cobalt hydride hydrogen atom transfer and radical-polar crossover mechanism enabled simultaneous cyclization and deprotection. The substrate scope was expanded by extensive optimization of the reaction conditions and tuning of the thioester unit. This is a rare instance of thioesters showing nucleophilic behavior. This method was also applicable to alkenyl selenoesters.

引用

页码：2039 / 2045

页数：13

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