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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 pro-nucleophiles 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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Publisher copy:
10.1002/anie.201410391

Authors


Oxford Skaggs More from this funder
Engineering and Physical Sciences Research Council More from this funder
Publisher:
Wiley Publisher's website
Journal:
Angewandte Chemie (International ed. in English) Journal website
Volume:
54
Issue:
5
Pages:
1642–1645
Publication date:
2014-12-01
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
Source identifiers:
499663
Language:
English
Keywords:
UUID:
uuid:4c3ccffd-bba0-4360-bade-2baec05578ee
Local pid:
pubs:499663
Deposit date:
2014-12-20

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