Work

Copper-Catalyzed Allylic Amination of Alkenes Using O -Acylhydroxylamines: A Direct Entry to Diverse N -Alkyl Allylamines

Year: 2025

Type: article

Abstract: We report a copper-catalyzed direct allylic amination of alkenes using readily available O -benzyolhydroxylamines as the alkylamine precursors and internal oxidant. A range of primary and secondary alkylamines can be installed onto diversely substituted alkenes for the rapid construction of N -alkyl allylamines. Mechanistic studies support that the reaction engages an initial electrophilic amination to alkenes with anti-Markovnikov selectivity and subsequently a regioselective oxidative elimination to furnish the double bond transposition. In the electrophilic amination step, the use of strong Brønsted acid is critical for generating the key aminium radical cation (ARC) species.

Source: ACS Catalysis

DOI: 10.1021/acscatal.5c01859

Authors: Eric J. McLaren, Guangshou Feng, Noah H. Watkins, Qiu Wang

Institution: Duke University

Language: English

Topic: Synthesis and Catalytic Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: American Chemical Society Petroleum Research Fund, National Institute of General Medical Sciences

Awards: New Methods for the Synthesis and Study of Bioactive Nitrogen-Containing Molecules, G5753153908, G5919408719