Aerobic Palladium‐Catalyzed Dioxygenation of Alkenes Enabled by Catalytic Nitrite1. (6th November 2014)

• Record Type: Journal Article
• Authors: Wickens, Zachary K.; Guzmán, Pablo E.; Grubbs, Robert H.
• Is Part Of: Angewandte Chemie. Volume 127:Number 1(2015)
• Page Start: 238
• Page End: 242
• Publication Date: 2014-11-06
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201408650
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Catalytic nitrite was found to enable carbon–oxygen bond‐forming reductive elimination from unstable alkyl palladium intermediates, providing dioxygenated products from alkenes. A variety of functional groups were tolerated, and high yields (up to 94 %) were observed with many substrates, also for a multigram‐scale reaction. Nitrogen dioxide, which could form from nitrite under the reaction conditions, was demonstrated to be a potential intermediate in the catalytic cycle. Furthermore, the reductive elimination event was probed with ¹⁸O‐labeling experiments, which demonstrated that both oxygen atoms in the difunctionalized products were derived from one molecule of acetic acid.</p> </abstract>