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Updated: Feb 9, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
SNAr-Derived Decomposition By-products Involving Pentafluorophenyl Triazolium Carbenes
Xiaodan Zhao1, Garrett S Glover1, Kevin M Oberg1
1Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
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 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.
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