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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Terminal-Selective sp3 C-H Borylation of Carbonyl Derivatives by a Di(pyridyl)arylmethane-Ligated Iridium Catalyst
Shuyao Zhang1, Taylor M Estock1, Nathan D Schley1
1Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States.
Abstract:
An iridium catalyst based on a 2,2'-dipyridylarylmethane ligand shows high activity at low catalyst loading for terminal sp3 C-H borylation of aliphatic carbonyl derivatives under conditions where the substrate is the limiting reagent. The site selectivity of the process is not directed by the functional group but, instead, by a preference for borylation of unhindered methyl groups over methylene or α-branched methyl groups. The active catalyst species are formed in situ from commercial precatalysts and a hydrosilane activator, with structural evidence provided by an isolable complex bearing a κ3-metalated ligand. The resulting alkylboronate esters are versatile reagents and are amenable to Pd-catalyzed B-alkyl Suzuki cross-coupling.
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