Gold(I) Carbenoids: On-Demand Access to Gold(I) Carbenes in Solution

Juan M Sarria Toro; Cristina García-Morales; Mihai Raducan; Ekaterina S Smirnova; Antonio M Echavarren

doi:10.1002/anie.201611705

Gold(I) Carbenoids: On-Demand Access to Gold(I) Carbenes in Solution

Angew Chem Int Ed Engl. 2017 Feb 6;56(7):1859-1863. doi: 10.1002/anie.201611705. Epub 2017 Jan 16.

Authors

Juan M Sarria Toro¹, Cristina García-Morales¹, Mihai Raducan¹, Ekaterina S Smirnova¹, Antonio M Echavarren^{1

2}

Affiliations

¹ Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
² Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/Marcel⋅li Domingo s/n, 43007, Tarragona, Spain.

Abstract

Chloromethylgold(I) complexes of phosphine, phosphite, and N-heterocyclic carbene ligands are easily synthesized by reaction of trimethylsilyldiazomethane with the corresponding gold chloride precursors. Activation of these gold(I) carbenoids with a variety of chloride scavengers promotes reactivity typical of metallocarbenes in solution, namely homocoupling to ethylene, olefin cyclopropanation, and Buchner ring expansion of benzene.

Keywords: Buchner reaction; carbenes; carbenoids; cyclopropanation; gold.

Publication types

Research Support, Non-U.S. Gov't