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Boron(III)‐Catalyzed C2‐Selective C−H Borylation of Heteroarenes
Author(s) -
Zhong Qi,
Qin Shengxiang,
Yin Youzhi,
Hu Jiajun,
Zhang Hua
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201808590
Subject(s) - borylation , pinacol , chemistry , regioselectivity , catalysis , thiophene , electrophilic substitution , pyrrole , combinatorial chemistry , indole test , boron , boronic acid , electrophile , medicinal chemistry , stereochemistry , organic chemistry , aryl , alkyl
A BF 3 ⋅Et 2 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 BF 3 ⋅Et 2 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.