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The enantioselective intermolecular sp(3) C-H functionalization at the allylic and benzylic positions was achieved using rhodium-catalyzed reactions with 4-phenyl-N-(methanesulfonyl)-1,2,3-triazole. The optimum dirhodium tetracarboxylate catalyst for these reactions was Rh2(S-NTTL)4. The rhodium-bound α-imino carbene intermediates preferentially reacted with tertiary over primary C-H bonds in good yields and moderate levels of enantioselectivity (66-82% ee). This work demonstrates that N-sulfonyltriazoles can be applied to the effective C-H functionalization at sp(3) C-H bonds of substrates containing additional functionality.

Enantioselective Intermolecular C–H Functionalization of Allylic and Benzylic sp3 C–H Bonds Using N-Sulfonyl-1,2,3-triazoles

Enantioselective Intermolecular C–H Functionalization of Allylic and Benzylic sp³ C–H Bonds Using N-Sulfonyl-1,2,3-triazoles