Hydrogen‐Borrowing and Interrupted‐Hydrogen‐Borrowing Reactions of Ketones and Methanol Catalyzed by Iridium1. Issue 5 (9th December 2014)

• Record Type: Journal Article
• Authors: Shen, Di; Poole, Darren L.; Shotton, Camilla C.; Kornahrens, Anne F.; Healy, Mark P.; Donohoe, Timothy J.
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 5(2015)
• Page Start: 1642
• Page End: 1645
• Publication Date: 2014-12-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201410391
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>