22077-56-1Relevant articles and documents
Synthesis of Diaryl Selenides via Palladium-Catalyzed Debenzylative Cross-Coupling of Aryl Benzyl Selenides with Aryl Bromides
Wang, Hao,Chen, Shuguang,Liu, Guoqing,Guan, Haixing,Zhong, Daoyin,Cai, Jun,Zheng, Zhipeng,Mao, Jianyou,Walsh, Patrick J.
supporting information, p. 4086 - 4091 (2018/11/21)
Herein, we report a novel method for synthesizing diaryl selenides from aryl benzyl selenides and aryl bromides via debenzylative cross-coupling with a Pd/NIXANTPHOS-catalyst. NIXANTPHOS outperformed other commonly used bi- and monodentate ligands examined in this novel transformation. This reaction system displays wide functional group tolerance and excellent substrate scope. The transformation broadens the scope of palladium-catalyzed debenzylative processes to use selenolate anions as a leaving group. Its potential for practical synthetic applications was demonstrated with the gram scale synthesis of 4-chlorophenyl phenyl selenide.
Diarylation of chalcogen elements using arylboronic acids via copper- or palladium-catalyzed oxidative coupling
Taniguchi, Nobukazu
, p. 5818 - 5823 (2016/08/30)
Transition metal-catalyzed diarylations of sulfur, selenium and tellurium were achieved using arylboronic acids in air. A copper-catalyzed reaction of sulfur or selenium efficiently yielded numerous symmetrical diaryl sulfides or selenides in the presence of NH4BF4. However, the diarylation of tellurium was not possible using this method, and required a palladium catalyst in the presence of KI and air for the reaction to proceed.
Copper-catalyzed chalcogenation of aryl iodides via reduction of chalcogen elements by aluminum or magnesium
Taniguchi, Nobukazu
, p. 10510 - 10515,6 (2012/12/12)
Aluminum-induced copper-catalyzed coupling of aryl iodides with selenium or sulfur element could afford the corresponding diaryl selenides or sulfides in good yields. When magnesium chloride as an additive was employed, diaryl monoselenides and monosulfides were selectively obtained. On the contrary, the use of sodium carbonate produced diaryl diselenides and disulfides. The preparation of diaryl diselenides was necessary for magnesium as a reductant. Regrettably, tellurium was very low reactivity.