High-Fidelity Transfer of Chiral Sulfonimidoyl Radicals

Radicals with intrinsic stereogenic and radical centers offer a promising yet largely unexplored platform for synthetic chemistry. We reported a family of chiral sulfonimidoyl radicals that enable stereoretentive radical transfer by using our bench-stable reagents. This approach unlocked switchable, modular access to enantioenriched sulfoximines or sulfinamides, avoiding the use of strong oxidants and organometallic nucleophiles. Additionally, mechanistic studies and computational investigations provide insightful and plausible explanations for the observed high fidelity of these underexplored chiral sulfonimidoyl radical species.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2026-05-19
DOI
https://doi.org/10.1021/jacs.6c06952
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

High-Fidelity Transfer of Chiral Sulfonimidoyl Radicals

Journal of the American Chemical Society
Radical Photochemical Reactions
article

High-Fidelity Transfer of Chiral Sulfonimidoyl Radicals

article en

Abstract

Radicals with intrinsic stereogenic and radical centers offer a promising yet largely unexplored platform for synthetic chemistry. We reported a family of chiral sulfonimidoyl radicals that enable stereoretentive radical transfer by using our bench-stable reagents. This approach unlocked switchable, modular access to enantioenriched sulfoximines or sulfinamides, avoiding the use of strong oxidants and organometallic nucleophiles. Additionally, mechanistic studies and computational investigations provide insightful and plausible explanations for the observed high fidelity of these underexplored chiral sulfonimidoyl radical species.

Journal of the American Chemical Society
Merck & Co., Inc., Rahway, NJ, USA (United States) (US), Southwestern Medical Center (US), Oberlin College (US), The University of Texas Southwestern Medical Center (US)
Welch Foundation, Camille and Henry Dreyfus Foundation, National Institutes of Health
Openalex Percentile: Top 9%
Radical Photochemical Reactions
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