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Photosensitizer‐Free Visible‐Light‐Mediated Gold‐Catalyzed 1,2‐Difunctionalization of Alkynes
Author(s) -
Huang Long,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201511487
Subject(s) - chemistry , aryl , catalysis , phosphine , photochemistry , denticity , combinatorial chemistry , photosensitizer , oxidative addition , pyridine , functional group , methanol , ligand (biochemistry) , salt (chemistry) , organic chemistry , alkyl , metal , biochemistry , polymer , receptor
Under visible‐light irradiation, the gold‐catalyzed intermolecular difunctionalization of alkynes with aryl diazonium salts in methanol affords a variety of α‐aryl ketones in moderate to good yields. In contrast to previous reports on gold‐catalyzed reactions that involve redox cycles, no external oxidants or photosensitizers are required. The reaction proceeds smoothly under mild reaction conditions and shows broad functional‐group tolerance. Further applications of this method demonstrate the general applicability of the arylation of a vinyl gold intermediate instead of the commonly used protodemetalation step. This step provides facile access to functionalized products in one‐pot processes. With a P,N‐bidentate ligand, a stable aryl gold(III) species was obtained, which constitutes the first direct experimental evidence for the commonly postulated direct oxidative addition of an aryl diazonium salt to a pyridine phosphine gold(I) complex.