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
收藏
页码：3691 / 3696
页数：6
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