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Zinc‐Catalyzed Dual C–X and C–H Borylation of Aryl Halides
Author(s) -
Bose Shubhankar Kumar,
Deißenberger Andrea,
Eichhorn Antonius,
Steel Patrick G.,
Lin Zhenyang,
Marder Todd B.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201505603
Subject(s) - borylation , halide , aryl , aryne , catalysis , chemistry , zinc , medicinal chemistry , group (periodic table) , photochemistry , combinatorial chemistry , organic chemistry , alkyl
A zinc‐catalyzed combined CX and CH borylation of aryl halides using B 2 pin 2 (pin=OCMe 2 CMe 2 O) to produce the corresponding 1,2‐diborylarenes under mild conditions was developed. Catalytic CH bond activation occurs ortho to the halide groups if such a site is available or meta to the halide if the ortho position is already substituted. This method thus represents a novel use of a group XII catalyst for CH borylation. This transformation does not proceed via a free aryne intermediate, but a radical process seems to be involved.