C,O-Chelated BINOL/Gold(III) Complexes: Synthesis and Catalysis with Tunable Product Profiles.

Angew Chem Int Ed Engl

State Key Laboratory of Chirosciences, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong, China.

Published: March 2017

Unprecedented stable BINOL/gold(III) complexes, adopting a novel C,O-chelation mode, were synthesized by a modular approach through combination of 1,1'-binaphthalene-2,2'-diols (BINOLs) and cyclometalated gold(III) dichloride complexes [(C^N)AuCl ]. X-ray crystallographic analysis revealed that the bidentate BINOL ligands tautomerized and bonded to the Au atom through C,O-chelation to form a five-membered ring instead of the conventional O,O'-chelation giving a seven-membered ring. These gold(III) complexes catalyzed acetalization/cycloisomerization and carboalkoxylation of ortho-alkynylbenzaldehydes with trialkyl orthoformates.

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http://dx.doi.org/10.1002/anie.201612243DOI Listing

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