Copper(II)-catalyzed aerobic oxidation of hydrazides to azo intermediates and their Diels–Alder versus ene trapping

Chaiyaveij, Duangduan; Whiting, Andrew

doi:10.24820/ark.5550190.p011.606

Copper(II)-catalyzed aerobic oxidation of hydrazides to azo intermediates and their Diels–Alder versus ene trapping

Chaiyaveij, Duangduan; Whiting, Andrew

Authors

Duangduan Chaiyaveij

Professor Andrew Whiting andy.whiting@durham.ac.uk
Emeritus Professor

Abstract

The oxidation of diethyl 1,2-hydrazinedicarboxylate using a catalytic Cu(II)-oxazoline system occurs at RT in air, resulting in azo generation, which can then be trapped in situ via hetero-Diels-Alder (HDA) and competitive ene-reactions, with chemoselectivity being both temperature and solvent dependent. The procedure was extended to other azo systems and mechanism studies are reported.

Citation

Chaiyaveij, D., & Whiting, A. (2021). Copper(II)-catalyzed aerobic oxidation of hydrazides to azo intermediates and their Diels–Alder versus ene trapping. ARKIVOC, 2021(10), 64-76. https://doi.org/10.24820/ark.5550190.p011.606

Journal Article Type	Article
Acceptance Date	Oct 11, 2021
Online Publication Date	Nov 7, 2021
Publication Date	2021
Deposit Date	Jan 31, 2022
Publicly Available Date	Feb 1, 2022
Journal	Arkivoc
Print ISSN	1551-7004
Publisher	ARKAT USA
Peer Reviewed	Peer Reviewed
Volume	2021
Issue	10
Pages	64-76
DOI	https://doi.org/10.24820/ark.5550190.p011.606

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