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Boron(III)-Catalyzed C2-Selective C-H Borylation of Heteroarenes

Boron(III)-Catalyzed C2-Selective C-H Borylation of Heteroarenes

Qi Zhong, Shengxiang Qin, Youzhi Yin, Jiajun Hu, Hua Zhang

Angew Chem Int Ed Engl. 2018 Nov 5;57(45):14891-14895.

PMID: 30203906

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP476004816	Indole-2-boronic acid pinacol ester		476004-81-6	Price

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