title: Rh2(II)-Catalyzed Ring Expansion of Cyclobutanol-Substituted Aryl Azides To Access Medium-Sized N-Heterocycles.
abstract: A new reactivity pattern of Rh2(II)-N-arylnitrenes was discovered that facilitates the synthesis of medium-sized N-heterocycles from ortho-cyclobutanol-substituted aryl azides. The key ring-expansion step of the catalytic cycle is both chemoselective and stereospecific. Our mechanistic experiments implicate the formation of a rhodium N-arylnitrene catalytic intermediate and reveal that sp3C-H bond amination of this electrophilic species is competitive with the ring-expansion process.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
authors.forename: Wrickban
authors.initials: W
authors.lastname: Mazumdar
authors.affiliation: Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
authors.forename: Navendu
authors.initials: N
authors.lastname: Jana
authors.affiliation: Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
authors.forename: Bryant T
authors.initials: BT
authors.lastname: Thurman
authors.affiliation: Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
authors.forename: Donald J
authors.initials: DJ
authors.lastname: Wink
authors.affiliation: Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.|Institute of Next Generation Matter Transformation, College of Chemical Engineering, Huaqiao University , 668 Jimei Boulevard, Xiamen, Fujian 361021, People's Republic of China.
authors.forename: Tom G
authors.identifier: http://orcid.org/0000-0001-7001-342X
authors.initials: TG
authors.lastname: Driver