Bronsted acid-catalyzed C6 functionalization of 2,3-disubstituted indoles for construction of cyano-substituted all-carbon quaternary centers

被引：0

作者：

Huang, Wen-Jun ^{[1
,2
]}

Liu, Li-Xia ^{[2
]}

Zhou, Yong-Gui ^{[2
]}

Wu, Bo ^{[2
]}

Jiang, Guo-Fang ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, Adv Catalyt Engineer Res Ctr, Minist Educ, Changsha 410082, Peoples R China

[2] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, 457 Zhongshan Rd, Dalian 116023, Liaoning, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 17期

基金：

中国国家自然科学基金;

关键词：

NATURAL-PRODUCTS; H FUNCTIONALIZATION; DRUG LEADS; 3-INDOLYLMETHANOLS; ALKYLATION; ALKALOIDS; ARYLATION; ACCESS;

D O I：

10.1039/d3ob00412k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a Bronsted acid-catalyzed C6 functionalization of 2,3-disubstituted indoles with 2,2-diarylacetonitriles for efficient construction of cyano-substituted all-carbon quaternary centers with excellent yields. The synthetic utility was demonstrated by the conversion of the cyano-group which enables the divergent preparation of aldehydes, primary amines and amides. Control experiments suggested that this process involves C-H oxidation of 2,2-diarylacetonitriles to in situ generate d,d-disubstituted p-quinone methide intermediates. This protocol provides an efficient method for C6 functionalization of 2,3-disubstituted indoles to construct all-carbon quaternary centers.

引用

页码：3691 / 3696

页数：6