Chelation-assisted C–C bond activation of biphenylene by gold(i) halides†

Received: 14 Feb 2021, Revised: 15 Feb 2021, Accepted: 10 June 2021, Available online: 18 June 2021, Version of Record: 18 June 2021

Hélène Beucher, ‡a , Johannes Schörgenhumer, ‡a , Estíbaliz Merino bc , and Cristina Nevado *a

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* Corresponding authors
a Department of Chemistry, University of Zurich, Winterthurerstrasse 190, Zurich, CH 8057, Switzerland
E-mail: cristina.nevado@chem.uzh.ch
b Universidad de Alcalá, Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Andrés M. del Río (IQAR), Facultad de Farmacia, Alcalá de Henares, Madrid, Spain
c Instituto Ramón y Cajal de Investigación Sanitaria (IRYCIS), Ctra. de Colmenar Viejo, Km. 9.100, Madrid, Spain

Abstract


A chelation-assisted oxidative addition of gold(I) into the C–C bond of biphenylene is reported here. The presence of a coordinating group (pyridine, phosphine) in the biphenylene unit enabled the use of readily available gold(I) halide precursors providing a new, straightforward entry towards cyclometalated (N^C^C)- and (P^C)-gold(III) complexes. Our study, combining spectroscopic and crystallographic data with DFT calculations, showcases the importance of neighboring, weakly coordinating groups towards the successful activation of strained C–C bonds by gold.
Graphical abstract: Chelation-assisted C–C bond activation of biphenylene by gold(i) halides



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