Transition-Metal-Free Redox-Neutral One-Pot C3-Alkenylation of lndoles Using Aldehydes

被引:29
作者
Sahu, Sarnrat [1 ]
Banerjee, Ankush [1 ]
Maji, Modhu Sudan [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India
关键词
DIELS-ALDER REACTION; INDOLE ALKALOIDS; CARBAZOLESPIROOXINDOLE SKELETONS; ASYMMETRIC ORGANOCATALYSIS; EFFICIENT SYNTHESIS; SYNTHETIC STRATEGY; BRONSTED ACIDS; ALKENYLATION; 3-VINYLINDOLES; DERIVATIVES;
D O I
10.1021/acs.orglett.6b03612
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of sensitive beta-alkyl 3-vinylindoles having diverse functional groups with good selectivity remains a challenging task. Keeping the synthetic utility of 3-alkenylindoles in mind, we explored a unique approach to synthesize them from unprotected indoles in a domino fashion. A transition-metal-free C3-alkenylation of indole is reported by using sequential Bronsted acid/base catalysis. Several beta-substituted 3-alkenylindoles and conjugated 1,3-dienes are synthesized by direct coupling of indole and readily available aliphatic aldehydes. Excellent scalability and recycling of benzenesulfinic acid for successive alkenylation reactions up to five times make this method economically viable.
引用
收藏
页码:464 / 467
页数:4
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