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Redox inversion: A radical analogue of umpolung reactivity for C(sp3)–C(sp3) bond formation

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

Abstract

The construction of alkyl–alkyl bonds is a powerful tool in organic synthesis. Redox inversion–defined as the radical analog of polarity inversion–is used as a strategy for C(sp3)–C(sp3) coupling. Herein is reported the photocatalytic coupling of carboxylic acids to form biologically relevant bibenzyls through redox inversion. A wide functional group tolerance is demonstrated in the scope. Additionally, mechanistic insight is gained through control reactions that implicate this new redox inversion strategy.

Keywords

umpolung
radicals
alkyl-alkyl coupling

Supplementary materials

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Version History

Aug 22, 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-qm9wx
D O I: 10.26434/chemrxiv-2022-qm9wx [opens in a new tab]

Funding

National Science Foundation
CHE-1954751

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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