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α-Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1-(Dialkylamino)-1,2,3-triazoles.

ABSTRACT: The one-pot synthesis of a series of sulfonium salts containing transferable diazomethyl groups is described, and the structure of these compounds is elucidated by X-ray crystallography. Under photochemical conditions, reaction of these salts with N,N-dialkyl hydrazones affords 1-(dialkylamino)-1,2,3-triazoles via diazomethyl radical addition to the azomethine carbon followed by intramolecular ring closure. The straightforward transformation of the structures thus obtained into mesoionic carbene-metal complexes is also reported and the donor properties of these new ligands characterized.

SUBMITTER: Li X

PROVIDER: S-EPMC8048477 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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α-Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1-(Dialkylamino)-1,2,3-triazoles.

Li Xiangdong X Golz Christopher C Alcarazo Manuel M

Angewandte Chemie (International ed. in English) 20210217 13

The one-pot synthesis of a series of sulfonium salts containing transferable diazomethyl groups is described, and the structure of these compounds is elucidated by X-ray crystallography. Under photochemical conditions, reaction of these salts with N,N-dialkyl hydrazones affords 1-(dialkylamino)-1,2,3-triazoles via diazomethyl radical addition to the azomethine carbon followed by intramolecular ring closure. The straightforward transformation of the structures thus obtained into mesoionic carbene ...[more]

PMID: 33351262

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