Sterically Directed Functionalization of Aromatic C−H Bonds: Selective Borylation Ortho to Cyano Groups in Arenes and Heterocycles
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- 12 July 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (30) , 10539-10544
- https://doi.org/10.1021/ja0428309
Abstract
Ir-catalyzed borylations of 4-substituted benzonitriles are described. In contrast to electrophilic aromatic substitutions and directed ortho metalations, C−H activation/borylation enables functionalization at the 2-position, adjacent to the cyano group, when the 4-subsitutent is larger than cyano. When an excess of borane reagent is used, diborylation can be achieved with a single regioisomer being formed in certain cases. Extension of sterically directed borylation to cyano-substituted, five- and six-membered ring heterocycles is also reported.Keywords
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