Metal-free B(C6F5)3 Catalyzed Regioselective Addition of Indole to Phenylacetylene

doi:10.7503/cjcu20180610

Abstract

Abstract: Catalytic amounts of B (C₆F₅)₃ was found to be able to catalyze the highly regioselective addition of various indoles to phenylacetylene,and produced different substituted bisindolylmethanes in high yields at room temperature.Contrast to the traditional catalysts such as In,Pt and Ru,B (C₆F₅)₃ finished the reaction under green and mild catalytic conditions with high atom economical and good functional group tolerance.Under the optimization reaction conditions,near quantitative conversions and up to 92% yields of bisindolylmethanes were achieved.According to the separated byproduct 4a' and the observed intermediates Ⅰ,a possible reaction mechanism based on the mechanistic studies has been proposed.The reaction was initiated from the activation of phenylacetylene by B (C₆F₅)₃ and ended with the addition of two molecules indoles one by one to the phenylacetylene.The further applied value research of bisindolylmethanes is in progress.

Key words: B(C₆F₅)₃, Indole, Regioselective addition, Bisindolylalkanes

CLC Number:

O621.25

TrendMD:

LIU Tianwei, ZHANG Sutao, HE Jianghua, ZHANG Yuetao. Metal-free B(C₆F₅)₃ Catalyzed Regioselective Addition of Indole to Phenylacetylene[J]. Chem. J. Chinese Universities, 2019, 40(4): 719.

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Metal-free B(C₆F₅)₃ Catalyzed Regioselective Addition of Indole to Phenylacetylene

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