Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, C-H Insertion, and Dimerization Reactions

Mesityl gold(I) carbenes lacking heteroatom stabilization or shielding ancillary ligands have been generated and spectroscopically characterized from chloro(mesityl)methylgold(I) carbenoids bearing JohnPhos-type ligands by chloride abstraction with GaCl3. The aryl carbenes react with PPh3 and alkenes to give stable phosphonium ylides and cyclopropanes, respectively. Oxidation with pyridine N- oxide and intermolecular C-H insertion to cyclohexane have also been observed. In the absence of nucleophiles, a bimolecular reaction, similar to that observed for other metal carbenes, leads to a symmetrical alkene.

García-Morales, C.; Pei, X. L.; Sarria Toro, J. M.; Echavarren, A. M.

Angew. Chem. Int. Ed. 2019, 58 (12), 3957-3961
DOI: 10.1002/anie.201814577

Associated ICIQ research group/s:

  • RESEARCH GROUP/S
    Prof. Antonio M. Echavarren
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