Yamamoto Yuki, Tanaka Ryo, Ota Miyuto, Nishimura Misaki, Tran Cong Chi, Kawaguchi Shin-Ichi, Kodama Shintaro, Nomoto Akihiro, Ogawa Akiya
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho Nakaku, Sakai, Osaka 599-8531, Japan.
Center for Education and Research in Agricultural Innovation, Faculty of Agriculture, Saga University, 152-1 Shonan-cho Karatsu, Saga 847-0021, Japan.
J Org Chem. 2020 Nov 20;85(22):14708-14719. doi: 10.1021/acs.joc.0c02014. Epub 2020 Oct 28.
The photoinduced reactions of tetraphenyldiphosphine disulfide with a range of organic dichalcogenides successfully afforded a series of phosphorus(V)-chalcogen interelement compounds via a radical process. The relative reactivities of the organic dichalcogenides (i.e., (PhS), (PhSe), and (PhTe)) toward the P or P groups in the diphosphine analogues under light were investigated in detail, and a convenient method was developed to form P-S or P-Se interelement compounds from tetraphenyldiphosphine disulfide and (PhS) or (PhSe) upon photoirradiation. Furthermore, the relative photochemical properties and reactivities of tetraphenyldiphophine (P-P interelement compound) and its analogues toward photoinduced radical addition reactions were also discussed. The formed P-E (E = S, Se) interelement compounds could be utilized for ionic reactions, and they could be transformed into various phosphine reagents via one-pot processes.
四苯基二膦二硫化物与一系列有机二硫属元素化物的光诱导反应通过自由基过程成功地得到了一系列磷（V）-硫属元素的元素间化合物。详细研究了有机二硫属元素化物（即（PhS）、（PhSe）和（PhTe））在光照下对二膦类似物中P或P基团的相对反应活性，并开发了一种简便的方法，通过光照射由四苯基二膦二硫化物和（PhS）或（PhSe）形成P-S或P-Se元素间化合物。此外，还讨论了四苯基二膦（P-P元素间化合物）及其类似物对光诱导自由基加成反应的相对光化学性质和反应活性。所形成的P-E（E = S，Se）元素间化合物可用于离子反应，并且可以通过一锅法转化为各种膦试剂。
