Potassium Hydroxide-Catalyzed Chemoselective Reduction of Cyclic Imides with Hydrosilanes: Synthesis of -Hydroxylactams and Lactams

被引：34

作者：

Ding, Guangni ^{[1
]}

Li, Chengjun ^{[1
]}

Shen, Yifan ^{[2
]}

Lu, Bin ^{[1
]}

Zhang, Zhaoguo ^{[1
,3
]}

Xie, Xiaomin ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

[2] Shanghai Jiao Tong Univ, Zhiyuan Coll, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

[3] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 08期

基金：

中国国家自然科学基金;

关键词：

base catalysis; cyclic imides; hydrosilylation; omega-hydroxylactams; lactams; CARBONYL-COMPOUNDS; SELECTIVE REDUCTION; SODIUM-BOROHYDRIDE; ASYMMETRIC HYDROSILYLATION; EFFICIENT HYDROSILYLATION; HETEROCYCLIC-SYSTEMS; MECHANISTIC ASPECTS; SECONDARY AMIDES; TERTIARY AMIDES; ARYL KETONES;

D O I：

10.1002/adsc.201501093

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Potassium hydroxide-catalyzed hydrosilylation exhibits excellent activity and chemoselectivity for the reduction of cyclic imides under mild reaction conditions. The chemoselectivity of the reduction system may be readily tuned by changing the identity and stoichiometry of the hydrosilanes: a polymethylhydrosiloxane (PMHS)/potassium hydroxide reduction system resulted in the reduction of various cyclic imides to the corresponding -hydroxylactams in 70-94% yield, while the diphenylsilane (Ph2SiH2)/potassium hydroxide reduction system selectively afforded the aryl lactams in 33-95% yield. These catalytic protocols tolerate diverse functional groups and are easy to scale up.

引用

页码：1241 / 1250

页数：10

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