Gold(III)- versus Gold(I)-Induced Cyclization: Synthesis of Six-Membered Mesoionic Carbene and Acyclic (Aryl)(Heteroaryl) Carbene Complexes

Authors

  • Gaël Ung,

    1. UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA 92093-0343 (USA)
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  • Dr. Michele Soleilhavoup,

    1. UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA 92093-0343 (USA)
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  • Prof. Guy Bertrand

    Corresponding author
    1. UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA 92093-0343 (USA)
    • UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA 92093-0343 (USA)
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  • The authors gratefully acknowledge financial support from the NIH (R01 GM 68825) and DOE (DE-FG02-09ER16069)

Abstract

original image

The golden state: Selective 5-exo- and 6-endo-cyclizations of an alkynyl benzothioamide have been achieved. The selectivity is controlled by the oxidation state of the gold precursor (+I or +III), yielding two new types of carbene ligand: an (aryl)(heteroaryl)carbene and a six-membered mesoionic carbene (see scheme). Mes=2,4,6-trimethylphenyl.

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