Divergent Synthesis of 3-Pyrrolidin-2-yl-1H-indoles, Symmetric and Unsymmetric Bis(Indolyl)Methanes (BIMs) through Photocatalyzed Decarboxylative Coupling/Friedel–Crafts Alkylation Reaction,The Journal of Organic Chemistry

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Divergent Synthesis of 3-Pyrrolidin-2-yl-1H-indoles, Symmetric and Unsymmetric Bis(Indolyl)Methanes (BIMs) through Photocatalyzed Decarboxylative Coupling/Friedel–Crafts Alkylation Reaction
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-03-07 , DOI: 10.1021/acs.joc.2c02166
Patamawadee Silalai ₁ , Rungnapha Saeeng ₁

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This paper reports the acid-controlled divergent synthesis of 3-pyrrolidin-2-yl-1H-indoles and symmetric and unsymmetrical bis(indolyl)methanes (BIMs) through photocatalyzed decarboxylative coupling and Friedel–Crafts alkylation reactions, respectively. The protocol involves C–H functionalization, switching formation of two products, room-temperature conditions, low photocatalyst loadings, without strong oxidant, and moderate to excellent yields. This method has been applied for the synthesis of natural product vibrindole A and 1,1-bis(1H-indol-3-yl)-2-phenylethane.

中文翻译：

3-Pyrrolidin-2-yl-1H-indoles、对称和不对称双（吲哚基）甲烷 (BIMs) 通过光催化脱羧偶联/Friedel-Crafts 烷基化反应的发散合成

本文分别报道了通过光催化脱羧偶联和 Friedel-Crafts 烷基化反应，酸控发散合成 3-pyrrolidin-2-yl-1 H-吲哚和对称和不对称双（吲哚基）甲烷 (BIM)。该协议涉及 C-H 功能化、两种产品的转换形成、室温条件、低光催化剂负载、无强氧化剂，以及中等到极好的收率。该方法已应用于天然产物vibrindole A和1,1-bis(1 H -indol-3-yl)-2-phenylethane的合成。

更新日期：2023-03-07

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