Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 127, Issue 30, Pages 10539-10544Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja0428309
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- NIGMS NIH HHS [GM63188] Funding Source: Medline
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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.
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