Divergent Synthesis of 3-Pyrrolidin-2-yl-1H-indoles, Symmetric and Unsymmetric Bis(Indolyl)Methanes (BIMs) through Photocatalyzed Decarboxylative Coupling/Friedel-Crafts Alkylation Reaction.
J Org Chem
; 88(7): 4052-4065, 2023 Apr 07.
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| MEDLINE
| ID: mdl-36881574
ABSTRACT
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.
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2023
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