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Distinct selectivity control in Cp*Co^III-catalyzed domino C–H activation/pyridine directing group migration/alkyne annulation has been accomplished through the nucleophilicity of an organometallic cobalt intermediate with a d⁶ electron configuration. Detailed mechanistic studies provided compelling evidence for a facile C–H activation along with a favorable migration of the directing group for the Cp*Co^III catalysis, rather than the β-oxygen elimination observed for a (CO)₃Mn^I manifold.