Conde Romina S, Torres Barroso Loydel, Pérez Edighill Sheila G, Yerien Damian E, Lantaño Beatriz, Baroncini Massimo, Barata-Vallejo Sebastian, Postigo Al
Departamento de Ciencias Químicas, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Buenos Aires CP 1113, Argentina.
Dipartimento di Scienze e Tecnologie Agro-alimentari, Università di Bologna, viale Fanin 44, 40127 Bologna, Italy.
J Org Chem. 2024 Aug 2;89(15):10867-10877. doi: 10.1021/acs.joc.4c01149. Epub 2024 Jul 21.
The synthesis of alkyl(aryl)-fluoroalkyl sulfanyl [R(Ar)-S-R] and aryl-fluoroalkyl selenolyl (Ar-Se-R) ethers through visible-light photocatalysis has been successfully carried out. This process involves disulfides, and diselenides [R(Ar)-X-X-R(Ar), where X = S or Se], and fluoroalkyl iodides (R-I) in the presence of a base as an additive under photocatalysis. The photocatalyst Eosin Y and green light-emitting diodes are utilized for irradiation of R(Ar)-S-R and Ar-Se-R syntheses. Our method integrates low-energy visible-light photocatalysis, commercially available perfluoroalkylating reagents (R-I), and easily obtainable disulfides and diselenides as starting materials. Mechanistic studies and a detailed synthetic procedure for (Ar)-S-R on a large scale are presented.
通过可见光光催化成功实现了烷基（芳基）-氟烷基硫烷基[R（Ar）-S-R]和芳基-氟烷基硒醇基（Ar-Se-R）醚的合成。该过程涉及在光催化下，在碱作为添加剂存在的情况下，使用二硫化物和二硒化物[R（Ar）-X-X-R（Ar），其中X = S或Se]以及氟代烷基碘化物（R-I）。光催化剂曙红Y和绿色发光二极管用于R（Ar）-S-R和Ar-Se-R合成的辐照。我们的方法整合了低能量可见光光催化、市售的全氟烷基化试剂（R-I）以及易于获得的二硫化物和二硒化物作为起始原料。本文介绍了机理研究以及大规模合成（Ar）-S-R的详细步骤。
