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




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Reference: Frost, JR, Cheong, CB, Akhtar, WM et al., (2015). Strategic application and transformation of ortho-disubstituted phenyl and cyclopropyl ketones to expand the scope of hydrogen borrowing catalysis. Journal of the American Chemical Society, 137 (50), 15664-15667.Citable link to this page:

 

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 carboxylic acid derivatives. In contrast, the cyclopropyl ketones underwent homoconjugate addition with several nucleophiles to provide further functionalized branched ketone products.

Peer Review status:Peer reviewedPublication status:PublishedVersion:Accepted manuscript Funder: Engineering and Physical Sciences Research Council   Funder: GlaxoSmithKline   Funder: Agency for Science, Technology and Research   Notes:Copyright © 2015 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.

Bibliographic Details

Publisher: American Chemical Society

Publisher Website: http://pubs.acs.org/

Journal: Journal of the American Chemical Societysee more from them

Publication Website: http://pubs.acs.org/journal/jacsat

Issue Date: 2015-12-11

pages:15664-15667Identifiers

Urn: uuid:fa318189-0412-4a07-967e-fb27177bf34d

Source identifier: 587298

Eissn: 1520-5126

Doi: https://doi.org/10.1021/jacs.5b11196

Issn: 0002-7863 Item Description

Type: Journal article;

Language: eng

Version: Accepted manuscript Tiny URL: pubs:587298

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Author: Frost, JR - institutionUniversity of Oxford Oxford, MPLS, Chemistry, Organic Chemistry - - - Cheong, CB - institutionUniversity o

Source: https://ora.ox.ac.uk/objects/uuid:fa318189-0412-4a07-967e-fb27177bf34d



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