Direct functionalization of inert C�H bonds to form new C�C bonds represents a long-standing challenge in both academic research and industrial processes. Although various catalytic C(sp2)�H bond functionalization methods have emerged during the past decade, the development of catalytic reactions involving direct and selective activation of C(sp3)�H bond is yet in its infancy. Recently we discovered a new class of direct C�H bond functionalization by which unactivated primary, secondary and tertiary C(sp3)�H bonds are effectively inserted into the p-bond of arynes generated from 1,3-diyne and alkyne via a metal-catalyzed formal intramolecular cycloaddition. The salient feature of this transformation is that multiple ring formation occurs in tandem manner and the C�H bond of an alkyl group tethered to arene is selectively cleaved. Initial catalyst screening showed that various silver salts as well as cationic ruthenium hydride complexes promote this transformation under mild reaction conditions. Studies on detailed reaction scope and mechanism will be demonstrated.

Metal-catalyzed functionalization of sp<sup>3</sup> C–H bond

244th National Meeting (2012)

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Metal-catalyzed functionalization of sp3 C–H bond

Metal-catalyzed functionalization of sp³ C–H bond