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Synfacts 2025; 21(01): 30
DOI: 10.1055/a-2467-4834
DOI: 10.1055/a-2467-4834
Synthesis of Materials and Unnatural Products
Seleno- and Telluroesters from Photoreactions of Acylsilanes
Masuda R,
*
Anami Y,
Kusama H.
*
Gakushuin University, Tokyo, Japan
Umpolung Synthesis of Selenoesters and Telluroesters via the Photoinduced Coupling of Acylsilanes with Electrophilic Chalcogen Reagents.
Org. Lett. 2024;
26: 8011-8016
DOI: 10.1021/acs.orglett.4c02757
Umpolung Synthesis of Selenoesters and Telluroesters via the Photoinduced Coupling of Acylsilanes with Electrophilic Chalcogen Reagents.
Org. Lett. 2024;
26: 8011-8016
DOI: 10.1021/acs.orglett.4c02757
Significance
A set of photochemical conditions are developed for synthesizing selenoesters and telluroesters, with a visible-light induced siloxycarbene intermediate suggested to react with electrophilic chalcogen reagents. The reaction exhibits a wide substrate scope.
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Comment
Through a series of control experiments, a plausible reaction mechanism is proposed, involving a photo-induced isomerization of an acylsilane, which undergoes nucleophilic attack on electrophilic selenium or tellurium reagents, prior to desilylation.
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Publication History
Article published online:
20 December 2024
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