Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N–H) Indoles via Common N-Indolyl Triethylborate

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• 作者：Zhi-Wei Zhang ; Hong Xue ; Hailing Li ; Huaiping Kang ; Juan Feng ; Aijun Lin ; Shouxin Liu
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：August 5, 2016
• 年：2016
• 卷：18
• 期：15
• 页码：3918-3921
• 全文大小：411K
• 年卷期：0
• ISSN：1523-7052

文摘

A general and direct C3 functionalization of free (N–H) indoles with readily available electrophiles such as acid chlorides, chloroformates, thionyl chloride, and methylsulfonyl chloride via a common N-indolyl triethylborate intermediate is reported. The reaction proceeds smoothly under mild conditions in up to 93% yield. Indoles with substituents at the C2, C4, C5, C6, and C7 positions are well tolerated. The easy accessibility of a variety of important 3-acylindoles, indole-3-carboxylic esters, indole-3-sulfinic acids, and 3-(methylsulfonyl)indoles demonstrates the high degree of compatibility and practicability of this method.