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Palladium-Catalyzed Decarbonylative C-H Difluoromethylation of Azoles
Frances Gu1, Naish Lalloo1, Emily R Wearing1
1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.
Abstract:
A (XantPhos)Pd-catalyzed decarbonylative C-H functionalization of azoles with difluoromethyl anhydrides is reported. Under the optimized conditions, azole substrates react selectively at the C(2)-position to afford CF2H-substituted benzoxazole, oxazole, benzothiazole, thiazole, and benzimidazole products. Organometallic mechanistic studies reveal that XantPhos enforces an unusual seesaw geometry of the key PdII(CF2H)(carboxylate) intermediate, which may be responsible for the effectiveness of this ligand.
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