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SET processes in Lewis acid-base reactions: the tritylation of N-heterocyclic carbenes.

ABSTRACT: Reactions between N-heterocyclic carbenes (NHCs) and the trityl cation, [Ph₃C]⁺, give covalent adducts of type [NHC-CPh₃]⁺ and/or [NHC-C₆H₅-CPh₂]⁺. EPR spectroscopy, UV-Vis analyses, and trapping experiments imply that adduct formation involves carbene radical cations and the trityl radical. The results demonstrate that single electron transfer (SET) processes should be considered for reaction of NHCs with oxidizing Lewis acids.

SUBMITTER: Dong Z

PROVIDER: S-EPMC8159480 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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SET processes in Lewis acid-base reactions: the tritylation of N-heterocyclic carbenes.

Dong Zhaowen Z Pezzato Cristian C Sienkiewicz Andrzej A Scopelliti Rosario R Fadaei-Tirani Farzaneh F Severin Kay K

Chemical science 20200409 29

Reactions between N-heterocyclic carbenes (NHCs) and the trityl cation, [Ph3C]+, give covalent adducts of type [NHC-CPh3]+ and/or [NHC-C6H5-CPh2]+. EPR spectroscopy, UV-Vis analyses, and trapping experiments imply that adduct formation involves carbene radical cations and the trityl radical. The results demonstrate that single electron transfer (SET) processes should be considered for reaction of NHCs with ox ...[more]

PMID: 34094138

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