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Polarity Transduction Enables the Formal Electronically Mismatched Radical Addition to Alkenes

Paul, Subhasis; Filippini, Dario; Silvi, Mattia

Polarity Transduction Enables the Formal Electronically Mismatched Radical Addition to Alkenes Thumbnail


Authors

Dario Filippini



Abstract

The formation of carbon-carbon bonds via the intermolecular addition of alkyl radicals to alkenes is a cornerstone of organic chemistry and plays a central role in synthesis. However, unless specific electrophilic radicals are involved, polarity matching requirements restrict the alkene component to be electron deficient. This limits the scope of a fundamentally important carbon-carbon bond forming process that could otherwise be more universally applied. Herein, we introduce a polarity transduction strategy that formally overcomes this electronic limitation. Vinyl sulfonium ions are demonstrated to react with carbon-centered radicals, giving adducts that undergo in situ or sequential nucleophilic displacement to provide products that would be inaccessible via traditional methods. The broad generality of this strategy is demonstrated through the derivatization of unmodified complex bioactive molecules.

Citation

Paul, S., Filippini, D., & Silvi, M. (2023). Polarity Transduction Enables the Formal Electronically Mismatched Radical Addition to Alkenes. Journal of the American Chemical Society, 145(5), 2773-2778. https://doi.org/10.1021/jacs.2c12699

Journal Article Type Article
Acceptance Date Nov 29, 2022
Online Publication Date Jan 31, 2023
Publication Date Feb 8, 2023
Deposit Date Mar 13, 2023
Publicly Available Date Mar 13, 2023
Journal Journal of the American Chemical Society
Print ISSN 0002-7863
Electronic ISSN 1520-5126
Publisher American Chemical Society (ACS)
Peer Reviewed Peer Reviewed
Volume 145
Issue 5
Pages 2773-2778
DOI https://doi.org/10.1021/jacs.2c12699
Keywords Colloid and Surface Chemistry; Biochemistry; General Chemistry; Catalysis
Public URL https://nottingham-repository.worktribe.com/output/16802361
Publisher URL https://pubs.acs.org/doi/10.1021/jacs.2c12699

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