Α, β-Dehydrogenation of esters with free OH and NH functionalities via allyl-palladium catalysis. Issue 26 (28th June 2018)

• Record Type: Journal Article
• Authors: Szewczyk, Suzanne M.; Zhao, Yizhou; Sakai, Holt A.; Dube, Pascal; Newhouse, Timothy R.
• Is Part Of: Tetrahedron. Volume 74:Issue 26(2018)
• Page Start: 3293
• Page End: 3300
• Publication Date: 2018-06-28
• Subjects: Allyl-palladium -- Dehydrogenation -- Esters -- β-Amino esters; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.02.028
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A direct and selective method for the α, β-dehydrogenation of esters using palladium catalysis in the presence of free OH and NH functionalities is reported herein. Allyl-palladium catalysis allows for preservation of readily oxidizable functionalities such as amines and alcohols. Furthermore, an economical protocol using LDA was developed for the dehydrogenation of β-amino esters. Graphical abstract: Image 1