title: SNAr-Derived Decomposition By-products Involving Pentafluorophenyl Triazolium Carbenes.
abstract: 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 theortho-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.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
authors.forename: Xiaodan
authors.initials: X
authors.lastname: Zhao
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
authors.forename: Garrett S
authors.initials: GS
authors.lastname: Glover
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
authors.forename: Kevin M
authors.initials: KM
authors.lastname: Oberg
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
authors.forename: Derek M
authors.initials: DM
authors.lastname: Dalton
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
authors.forename: Tomislav
authors.initials: T
authors.lastname: Rovis
keywords: Pentafluorophenyl N-heterocyclic carbene; decomposition; inner salt; spirocyclic oxindole