ol6b01298_si_001.pdf (6.12 MB)
Enantioselective Intermolecular C–H Functionalization of Allylic and Benzylic sp3 C–H Bonds Using N‑Sulfonyl-1,2,3-triazoles
journal contribution
posted on 2016-06-22, 17:03 authored by Robert
W. Kubiak, Jeffrey D. Mighion, Sidney M. Wilkerson-Hill, Joshua S. Alford, Tetsushi Yoshidomi, Huw M. L. DaviesThe
enantioselective intermolecular sp3 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 sp3 C–H bonds of substrates
containing additional functionality.