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Hydrogen-borrowing and interrupted-hydrogen-borrowing reactions of ketones and methanol catalyzed by iridium

Abstract:
Reported herein is the use of catalytic [{Ir(cod)Cl}2] to facilitate hydrogen-borrowing reactions of ketone enolates with methanol at 65°C. An oxygen atmosphere accelerates the process, and when combined with the use of a bulky monodentate phosphine ligand, interrupts the catalytic cycle by preventing enone reduction. Subsequent addition of pronucleophiles to the reaction mixture allowed a one-pot methylenation/conjugate addition protocol to be developed, which greatly expands the range of products that can be made by this methodology.
Publication status:
Published
Peer review status:
Peer reviewed

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MSD
Department:
Biochemistry
Role:
Author
Publisher:
Wiley
Journal:
Angewandte Chemie - International Edition More from this journal
Volume:
54
Issue:
5
Pages:
1642-1645
Publication date:
2015-01-26
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
Keywords:
Pubs id:
pubs:506130
UUID:
uuid:b1fa6879-e31b-40be-a371-912f5fdae19f
Local pid:
pubs:506130
Source identifiers:
506130
Deposit date:
2015-07-10

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