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Formation of Aryl‐ and Benzylboronate Esters by Rhodium‐Catalyzed C−H Bond Functionalization with Pinacolborane
Author(s) -
Shimada Shigeru,
Batsanov Andrei S.,
Howard Judith A. K.,
Marder Todd B.
Publication year - 2001
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 - 10.1002/1521-3773(20010601)40:11<2168::aid-anie2168>3.0.co;2-0
Subject(s) - mesitylene , borylation , chemistry , toluene , catalysis , rhodium , aryl , homogeneous , surface modification , medicinal chemistry , selectivity , organic chemistry , alkyl , physics , thermodynamics
Direct borylation of C−H bonds in aromatic compounds can be achieved by using the efficient homogeneous catalyst precursor [RhCl(P i Pr 3 ) 2 (N 2 )] and pinacolborane (HBpin; see scheme). High selectivity for the benzyl positions, observed for toluene, p ‐xylene, and mesitylene, was attributed to the formation of η 3 ‐benzyl intermediates.