Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 14, Pages 3747-3756Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00383j
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Funding
- National Natural Science Foundation of China [21971081, 22171099, 21820102003, 91956201]
- Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University [2021YB02]
- Program of Introducing Talents of Discipline to Universities of China (111 Program) [B17019]
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This study reports a convenient strategy utilizing visible-light-driven proton-coupled electron transfer to decompose sulfur ylides into carbon radicals, enabling the construction of 1,2-hydroxyacylmethylation reactions. The method achieves high selectivity and demonstrates a wide range of applicability, shedding light on the mechanism and regioselectivity origin.
The utilization of the zwitterionic properties of sulfur ylides has long been known to be a versatile strategy used in a wide range of chemical transformations for the construction of different-sized rings. By contrast, their use in radical synthetic chemistry has been significantly limited due to a dearth of general activation methods. Herein, a convenient visible-light-driven proton-coupled electron transfer strategy that enables sulfur ylides to decompose into their corresponding alpha-carbonyl carbon radicals is reported. Utilizing this strategy, highly selective 1,2-hydroxyacylmethylation between 1,3-dienes, sulfur ylides, and water under the action of photoredox catalysis is achieved (>40 examples are shown). Preliminary mechanistic studies and theoretical calculations shed light on the mechanism and the origin of the regioselectivity.
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