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

Chaiyaveij, Duangduan; Whiting, Andrew

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
• Electronic ISSN: 1551-7012
• Publisher: ARKAT USA
• Peer Reviewed: Peer Reviewed
• Volume: 2021
• Issue: 10
• Pages: 64-76
• DOI: https://doi.org/10.24820/ark.5550190.p011.606
• Public URL: https://durham-repository.worktribe.com/output/1218061