title: Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes.
abstract: Readily available 1-mesyl-1,2,3-triazoles are efficiently converted into a variety of imidazolones and thiazoles by Rh(II)-catalyzed denitrogenative reactions with isocyanates and isothiocyanates, respectively. The proposed triazole-diazoimine equilibrium results in the formation of highly reactive azavinyl metal-carbenes, which react with heterocumulenes causing an apparent swap of 1,2,3-triazole core for another heterocycle.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Stepan
authors.initials: S
authors.lastname: Chuprakov
authors.forename: Sen Wai
authors.initials: SW
authors.lastname: Kwok
authors.forename: Valery V
authors.initials: VV
authors.lastname: Fokin
mesh_terms: D002384:Catalysis; D007093:Imidazoles / Q000737:chemistry; D017953:Isocyanates / Q000737:chemistry; D017879:Isothiocyanates / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D011090:Polyenes / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry; D013441:Sulfinic Acids / Q000737:chemistry*; D013844:Thiazoles / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*
chemical_list: D007093:Imidazoles; D017953:Isocyanates; D017879:Isothiocyanates; D011090:Polyenes; D013441:Sulfinic Acids; D013844:Thiazoles; D014230:Triazoles; C117197:imidazolone; C030011:carbene; C037152:isothiocyanic acid; D012238:Rhodium; D008697:Methane