Carbene-Catalyzed Indole 3-Methyl C(sp3)-H Bond Functionalization

被引：21

作者：

Cheng, Jian ^{[1
]}

Sun, Jun ^{[1
]}

Yan, Jiekuan ^{[1
]}

Yang, Song ^{[1
]}

Zheng, Pengcheng ^{[1
]}

Jian, Zhichao ^{[1
]}

Chi, Yonggui Robin ^{[1
,2
]}

机构：

[1] Guizhou Univ, Minist Educ, Key Lab Green Pesticide & Agr Bioengn, Lab Breeding Base Green Pesticide & Agr Bioengn, Guiyang 550025, Guizhou, Peoples R China

[2] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 24期

基金：

中国国家自然科学基金; 新加坡国家研究基金会;

关键词：

DIELS-ALDER REACTIONS; ALPHA; BETA-UNSATURATED ALDEHYDES; GAMMA-BUTYROLACTONES; DOMINO REACTIONS; ORGANOCATALYSIS; ACTIVATION; ACID; HETEROCYCLES; CYCLIZATION; POLYMERASE;

D O I：

10.1021/acs.joc.7b02436

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The metal-free catalytic functionalization of aromatic sp(2)-carbons and benzylic spa-carbons remains challenging. Here we report a carbene-catalyzed functionalization of the 3-methyl sp(3)-carbon attached to 2-formyl-indoles. The reaction proceeds through an NHC-bound o-quinodimethane as the key intermediate generated from 2-formyl-3-methylindoles under oxidative conditions. Reactive ketones are found to be effective substrates to produce substituted hydropyrano[3,4-b]indoles in good to excellent yields.

引用

页码：13342 / 13347

页数：6

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