biostudies-literatureUnknown24(10)Zhao XPentafluorophenyl triazolium carbenes, widely used in NHC-catalysis, can decompose by several mechanisms. Under high concentration conditions, the azolium may undergo a pentafluorophenyl exchange by a proposed SNAr mechanism to give an inactive salt. In the presence of appropriate substrates, cyclization on the ortho-position of the arene can occur, also by SNAr. These adducts provide a potential pathway for catalyst decomposition and serve as a caveat to the development of new reactions and catalysts.Synlett : accounts and rapid communications in synthetic organic chemistryhttps://www.ebi.ac.uk/biostudies/studies/S-EPMC3873771biostudies-literatureSNAr-Derived Decomposition By-products Involving Pentafluorophenyl Triazolium Carbenes.PMC3873771Dalton DMOberg KMRovis TZhao XGlover GSfalseSNAr-Derived Decomposition By-products Involving Pentafluorophenyl Triazolium Carbenes.Pentafluorophenyl triazolium carbenes, widely used in NHC-catalysis, can decompose by several mechanisms. Under high concentration conditions, the azolium may undergo a pentafluorophenyl exchange by a proposed SNAr mechanism to give an inactive salt. In the presence of appropriate substrates, cyclization on the ortho-position of the arene can occur, also by SNAr. These adducts provide a potential pathway for catalyst decomposition and serve as a caveat to the development of new reactions and catalysts.2013-01-01T00:00:00Z2013 Jun2024-11-06T04:10:13.291Z2019-03-27T01:19:03ZS-EPMC38737712437952210.1055/s-0033-1338842