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- Title
Hydrogen-Borrowing and Interrupted-Hydrogen-Borrowing Reactions of Ketones and Methanol Catalyzed by Iridium.
- Authors
Shen, Di; Poole, Darren L.; Shotton, Camilla C.; Kornahrens, Anne F.; Donohoe, Timothy J.; Healy, Mark P.
- 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.
- Subjects
CATALYTIC activity; IRIDIUM catalysts; MICHAEL reaction; KETONES; METHANOL; ALKYLATION kinetics; BAEYER-Villiger rearrangement
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 5, p1642
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201410391