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The B(C6F5)3·H2O promoted synthesis of fluoroalkylated 3,3′,3′′-trisindolylmethanes from fluorocarboxylic acids and indoles†
Xin Xu,Dandan Gao,Jiahua Wang,Xiang-Ying Tang,Long Wang
Organic & Biomolecular Chemistry Pub Date : 01/09/2023 00:00:00 , DOI:10.1039/D2OB02241A
Abstract

Trisindolylmethanes (TIMs) exist in many bioactive natural products and are frequently applied in medicinal chemistry and materials science. Herein, a simple and efficient protocol promoted by B(C6F5)3·H2O for the synthesis of their fluoroalkylated analogues, fluoroalkylated 3,3′,3′′-TIMs, is reported for the first time. Easily accessible fluorocarboxylic acids are utilized as the fluoroalkyl sources, exhibiting an obvious fluorine effect. This convenient and green process features mild and metal-free conditions, easy scale-up, and an environmentally friendly byproduct.

Graphical abstract: The B(C6F5)3·H2O promoted synthesis of fluoroalkylated 3,3′,3′′-trisindolylmethanes from fluorocarboxylic acids and indoles
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