Nickel/N-Heterocyclic Carbene Complex-Catalyzed Enantioselective Redox-Neutral Coupling of Benzyl Alcohols and Alkynes to Allylic Alcohols

被引：86

作者：

Cai, Yuan ^{[1
]}

Zhang, Jia-Wen ^{[1
]}

Li, Feng ^{[1
]}

Liu, Jia-Ming ^{[1
]}

Shi, Shi-Liang ^{[1
]}

机构：

[1] Univ Chinese Acad Sci, Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem,Ctr Excellence Mo, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ACS CATALYSIS | 2019年 / 9卷 / 01期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; nickel; ligand design; N-heterocyclic carbenes; transfer hydrogenation; redox-neutral coupling; alkynes; alcohols; C-H FUNCTIONALIZATION; TRANSFER HYDROGENATION; ASYMMETRIC-SYNTHESIS; CARBONYL ALLYLATION; BOND FORMATION; ALDEHYDES; LIGAND; CROTYLATION; VINYLATION; OLEFINS;

D O I：

10.1021/acscatal.8b04198

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：

The nickel-catalyzed enantioselective redox-neutral coupling of alcohols and alkynes to access chiral allylic alcohols is reported. The reaction proceeds via a hydrogen transfer process under ambient temperature, converting abundant feedstock alcohols and alkynes to chiral allylic alcohols with high stereoselectivities in one chemical step. Key to the success of this process was the development of a bulky chiral N-heterocyclic carbene, (R,R,R,R)-SIPE, a chiral version of SIPr, as the ligand for nickel. Notably, we found that the utilization of P(OPh)(3) as secondary ligand for nickel was crucial to inhibit the isomerization of products.

引用

页码：1 / 6

页数：11

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