title: Enantioselective Intermolecular C-H Functionalization of Allylic and Benzylic sp(3) C-H Bonds Using N-Sulfonyl-1,2,3-triazoles.
abstract: 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.
authors.affiliation: Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
authors.forename: Robert W
authors.initials: RW
authors.lastname: Kubiak
authors.affiliation: Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: Mighion
authors.affiliation: Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
authors.forename: Sidney M
authors.initials: SM
authors.lastname: Wilkerson-Hill
authors.affiliation: Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
authors.forename: Joshua S
authors.initials: JS
authors.lastname: Alford
authors.affiliation: Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa , Nagoya 464-8602, Japan.|Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa , Nagoya 464-8602, Japan.
authors.forename: Tetsushi
authors.initials: T
authors.lastname: Yoshidomi
authors.affiliation: Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
authors.forename: Huw M L
authors.initials: HM
authors.lastname: Davies
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis*; D002384:Catalysis; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
chemical_list: D001555:Benzene Derivatives; D013441:Sulfinic Acids; D014230:Triazoles; D012238:Rhodium