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Boron(III)-Catalyzed C2-Selective C-H Borylation of Heteroarenes
Qi Zhong1, Shengxiang Qin1, Youzhi Yin1
1College of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang, 330031, P. R. China.
Abstract:
A BF3 ⋅Et2 O-catalyzed C2-selective C-H borylation of indoles with bis(pinacolato)diboron was developed to afford indole-2-boronic acid pinacol esters. A variety of functional groups were tolerated, and other heteroarenes like pyrrole and benzo[b]thiophene were also suitable substrates. An electrophilic substitution mechanism was proposed based on the preliminary mechanistic studies. This novel transformation utilizes simple and cheap BF3 ⋅Et2 O as catalyst and exhibits unusual C2 regioselectivity, providing a significant non-transition-metal-catalyzed C-H borylation and an efficient method towards the synthesis of C2-functionalized heteroarenes.
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