Tuning the Catalyst Reactivity of lmidazolylidene Catalysts through Substituent Effects on the N-Aryl Groups

被引：16

作者：

Kyan, Ryuji ^{[1
]}

Sato, Kohei ^{[1
]}

Mase, Nobuyuki ^{[1
,2
]}

Watanabe, Naoharu ^{[3
]}

Narumi, Tetsuo ^{[1
,2
]}

机构：

[1] Shizuoka Univ, Grad Sch Integrated Sci & Technol, Dept Engn, 3-5-1 Johoku, Hamamatsu, Shizuoka 4328561, Japan

[2] Shizuoka Univ, Res Inst Green Sci & Technol, 3-5-1 Johoku, Hamamatsu, Shizuoka 4328561, Japan

[3] Shizuoka Univ, Grad Sch Sci & Technol, 3-5-1 Johoku, Hamamatsu, Shizuoka 4328561, Japan

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 10期

关键词：

HETEROCYCLIC CARBENES; GAMMA-BUTYROLACTONES; STEREOSELECTIVE-SYNTHESIS; COOPERATIVE CATALYSIS; DIRECT ANNULATIONS; ENALS; ALDEHYDES; HOMOENOLATE; LACTONES; UMPOLUNG;

D O I：

10.1021/acs.orglett.7b01105

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of imidazolium salts with various N-aryl groups were synthesized, and their catalytic activities were evaluated to investigate the contribution of the N-aryl groups to the catalytic activity in the synthesis of gamma-butyrolactone through an a(3)-> d(3)-umpolung addition. Imidazolylidenes with 2,6-diethylphenyl groups were effective catalysts, and several mechanistic studies, including a deuterium kinetic isotope effect study, revealed that both steric and kinetic effects were responsible for the enhanced catalytic activity.

引用

页码：2750 / 2753

页数：4

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