Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 22, Pages 8157-8160Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja403462b
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Funding
- NSF [CHE-1156496]
- Direct For Mathematical & Physical Scien [1213409] Funding Source: National Science Foundation
- Division Of Chemistry [1213409] Funding Source: National Science Foundation
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Most functionalizations of C-H bonds by main-group reagents occur at aryl or methyl groups. We describe a highly regioselective borylation of secondary benzylic C-H bonds catalyzed by an iridium precursor and 3,4,7,8-tetramethyl-1,10-phenanthroline as the ligand. The reaction is directed to the benzylic position by a hydrosilyl substituent. This hydrosilyl directing group is readily deprotected or transformed to other functional groups after the borylation reaction, providing access to a diverse set of secondary benzylboronate esters by C-H borylation chemistry.
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