Design of an Indolylphosphine Ligand for Reductive Elimination-Demanding Monoarylation of Acetone Using Aryl Chlorides

The rational design of a phosphine ligand for the reductive elimination-demanding Pd-catalyzed mono-α-arylation of acetone is demonstrated and reported. The catalyst is tolerant of previously proven challenging electron-deficient aryl chlorides and provides excellent product yields with down to 0.1...

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Bibliographic Details
Published in:Organic letters 2015-09, Vol.17 (18), p.4612-4615
Main Authors: Fu, Wai Chung, So, Chau Ming, Chow, Wing Kin, Yuen, On Ying, Kwong, Fuk Yee
Format: Article
Language:English
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Summary:The rational design of a phosphine ligand for the reductive elimination-demanding Pd-catalyzed mono-α-arylation of acetone is demonstrated and reported. The catalyst is tolerant of previously proven challenging electron-deficient aryl chlorides and provides excellent product yields with down to 0.1 mol % Pd. Preliminary investigations suggest that the rate-limiting step for the proposed system is the oxidative addition of aryl chlorides, in which it contradicts previous findings regarding the α-arylation of acetone with aryl halides.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02344