Strategic Application and Transformation of ortho-Disubstituted Phenyl and Cyclopropyl Ketones To Expand the Scope of Hydrogen Borrowing Catalysis | Zendy

James R. Frost | Zendy; Choon Boon Cheong | Zendy; Wasim M. Akhtar | Zendy; Dimitri F. J. Caputo | Zendy; Neil G. Stevenson | Zendy; Timothy J. Donohoe | Zendy

Open Access

Strategic Application and Transformation of ortho-Disubstituted Phenyl and Cyclopropyl Ketones To Expand the Scope of Hydrogen Borrowing Catalysis

Author(s) -

James R. Frost,

Choon Boon Cheong,

Wasim M. Akhtar,

Dimitri F. J. Caputo,

Neil G. Stevenson,

Timothy J. Donohoe

Publication year - 2015

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.5b11196

Subject(s) - chemistry , ketone , catalysis , nucleophile , acylation , iridium , friedel–crafts reaction , carboxylic acid , organic chemistry , hydrogen bond , combinatorial chemistry , medicinal chemistry , molecule

The application of an iridium-catalyzed hydrogen borrowing process to enable the formation of α-branched ketones with higher alcohols is described. In order to facilitate this reaction, ortho-disubstituted phenyl and cyclopropyl ketones were recognized as crucial structural motifs for C-C bond formation. Having optimized the key catalysis step, the ortho-disubstituted phenyl products could be further manipulated by a retro-Friedel-Crafts acylation reaction to produce synthetically useful carboxylic acid derivatives. In contrast, the cyclopropyl ketones underwent homoconjugate addition with several nucleophiles to provide further functionalized branched ketone products.

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