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C,O‐Chelated BINOL/Gold(III) Complexes: Synthesis and Catalysis with Tunable Product Profiles
Author(s) -
Cui JianFang,
Ko HokMing,
Shing KaPan,
Deng JieRen,
Lai Nathanael ChunHim,
Wong ManKin
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201612243
Subject(s) - cycloisomerization , chelation , chemistry , denticity , ring (chemistry) , catalysis , medicinal chemistry , stereochemistry , combinatorial chemistry , crystallography , organic chemistry , crystal structure
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 2 ]. X‐ray crystallographic analysis revealed that the bidentate BINOL ligands tautomerized and bonded to the Au III 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.