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Transition metal-free intramolecular hydride transfer onto arynes is reported for the first time. This unique transformation is utilized in redox-neutral intermolecular α-functionalization reactions of different tertiary amines, generating C(sp 3 )-C(sp 3 /sp 2 /sp) bonds in a single synthetic operation. Deuterium labeling studies support initial cleavage of the α-C-H bond via intramolecular 1,5-hydride transfer onto the aryne, which leads to activation of a range of integrated pronucleophiles and ultimately affords a new approach to cross-dehydrogenative coupling reactions which utilize aryne intermediates.

Intramolecular hydride transfer onto arynes: redox-neutral and transition metal-free C(sp3)–H functionalization of amines

Intramolecular hydride transfer onto arynes: redox-neutral and transition metal-free C(sp³)–H functionalization of amines