Stewart Shea, Maloney Robert, Sun Yugang
Department of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, Pennsylvania 19122, USA.
Chem Commun (Camb). 2023 Mar 21;59(24):3546-3549. doi: 10.1039/d3cc00001j.
Triphenylphosphine oxide (TPPO) and triphenylphosphine (TPP) can form a complex in solution, promoting visible light absorption to trigger electron transfer within the complex and generate radicals. Subsequent radical reactions with thiols enable desulfurization to produce carbon radicals that react with aryl alkenes to yield new C-C bonds. Since ambient oxygen can easily oxidize TPP to TPPO, the reported method requires no explicit addition of a photocatalyst. This work highlights the promise of using TPPO as a catalytic photo-redox mediator in organic synthesis.
三苯基氧化膦(TPPO)和三苯基膦(TPP)在溶液中可形成络合物,促进对可见光的吸收,引发络合物内的电子转移并产生自由基。随后,自由基与硫醇发生反应实现脱硫,生成碳自由基,该碳自由基与芳基烯烃反应形成新的C-C键。由于环境中的氧气可轻易将TPP氧化为TPPO,因此所报道的方法无需明确添加光催化剂。这项工作凸显了将TPPO用作有机合成中催化光氧化还原介质的前景。