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Formal gamma-C(sp3)–H Activation of Ketones via Microwave-Promoted and Iminyl-Radical-Mediated 1,5-Hydrogen Atom Transfer

27 September 2022, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Microwave irradiation of O-phenyloximes triggers N–O homolysis and 1,5-hydrogen atom transfer (HAT), resulting in formal gamma-C–H functionalization of ketones after trapping of the radical intermediate and in situ imine hydrolysis. The Lewis acid InCl3∙H2O facilitated the HAT step, enabling functionalization of nonbenzylic 1° carbon atoms. Both C–O and C–C bond formation could be accomplished by this method.

Keywords

iminyl radicals
C-H functionalization
microwave-promoted reactions

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Version History

Sep 27, 2022 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-04hsj
D O I: 10.26434/chemrxiv-2022-04hsj [opens in a new tab]

Funding

National Science Foundation
CHE-1856530
National Science Foundation
CHE-1757627

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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