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Strategic application and transformation of ortho-disubstituted phenyl and cyclopropyl ketones to expand the scope of hydrogen borrowing catalysis.

Abstract:

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 carb...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted manuscript

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Publisher copy:
10.1021/jacs.5b11196

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Stevenson, NG More by this author
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GlaxoSmithKline More from this funder
Agency for Science, Technology and Research More from this funder
Publisher:
American Chemical Society Publisher's website
Journal:
Journal of the American Chemical Society Journal website
Volume:
137
Issue:
50
Pages:
15664-15667
Publication date:
2015-12-11
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:fa318189-0412-4a07-967e-fb27177bf34d
Source identifiers:
587298
Local pid:
pubs:587298
Language:
English

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