Issue 9, 2017

Transition-metal-free dehydrogenation coupling of pyridinium through a self-promoted hydride transfer process

Abstract

A transition-metal-free intramolecular cross dehydrogenation coupling reaction of pyridinium was developed. The C(sp2)–H/C(sp2)–H coupling reaction involved an unprecedented intermolecular hydride transfer process from the 1,2-dihydropyridine intermediate to another molecule of pyridinium and formed 1,4-dihydropyridine. Unlike the well-known dehydrogenation coupling proceeded under oxidative conditions, this was the first example of the coupling reaction through a substrate self-promoted hydride transfer process.

Graphical abstract: Transition-metal-free dehydrogenation coupling of pyridinium through a self-promoted hydride transfer process

Supplementary files

Article information

Article type
Research Article
Submitted
18 Cam 2017
Accepted
08 Wax 2017
First published
12 Wax 2017

Org. Chem. Front., 2017,4, 1789-1793

Transition-metal-free dehydrogenation coupling of pyridinium through a self-promoted hydride transfer process

W. Shang, S. Li, Y. Ding, Z. Pan, X. Tong and C. Xia, Org. Chem. Front., 2017, 4, 1789 DOI: 10.1039/C7QO00389G

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