86317-56-8Relevant articles and documents
Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions
Castoldi, Laura,Di Tommaso, Ester Maria,Gr?fen, Barbara,Olofsson, Berit,Reitti, Marcus
supporting information, p. 15512 - 15516 (2020/06/23)
The iodine(III) reagents vinylbenziodoxolones (VBX) were employed to vinylate a series of aliphatic and aromatic thiols, providing E-alkenyl sulfides with complete chemo- and regioselectivity, as well as excellent stereoselectivity. The methodology displays high functional group tolerance and proceeds under mild and transition metal-free conditions without the need for excess substrate or reagents. Mercaptothiazoles could be vinylated under modified conditions, resulting in opposite stereoselectivity compared to previous reactions with vinyliodonium salts. Novel VBX reagents with substituted benziodoxolone cores were prepared, and improved reactivity was discovered with a dimethyl-substituted core.
Visible light initiated hydrothiolation of alkenes and alkynes over ZnIn2S4
Li, Yuanyuan,Cai, Jingyu,Hao, Mingming,Li, Zhaohui
, p. 2345 - 2351 (2019/05/21)
The construction of C-S bonds is very important. The hydrothiolation of alkenes or alkynes with thiols represents an attractive and atom economical approach for the formation of C-S bonds. In this manuscript, flowerlike microspheres of ZnIn2S4 consisting of interweaving nanoflakes were prepared by a solvothermal method and were applied for the first time in the visible light initiated hydrothiolation of alkenes and alkynes. The reactions between a broad range of thiols and alkynes or alkenes over irradiated ZnIn2S4 afford the corresponding hydrothiolated products in moderate to excellent yields. The mechanism proposed based on the ESR results suggests that the holes generated over irradiated ZnIn2S4 are reductively quenched by the thiols to generate thiyl radicals, which are added to the alkynes/alkenes to generate alkene/alkyl radicals for the propagation of thiol-ene/thiol-yne coupling reactions. The use of solar light and a semiconductor-based photocatalyst to realize the thiol-ene and thiol-yne coupling reactions in a green solvent (methanol), with only stoichiometric thiols required and applicable to a broad substrate scope, makes this reaction protocol a green, sustainable and cost-effective strategy for the synthesis of thiolated products. This study also highlights the great potential of semiconductor-based photocatalysis for advanced organic syntheses.
Regioselective hydrothiolation of terminal acetylene catalyzed by magnetite (Fe3O4) nanoparticles
Rocha, Manuela S. T.,Rafique, Jamal,Saba, Sumbal,Azeredo, Juliano B.,Back, Davi,Godoi, Marcelo,Braga, Antonio L.
supporting information, p. 291 - 298 (2017/02/10)
Herein, we report a new and solvent-free methodology for the preparation of vinyl thioethers from terminal alkynes and thiols, using magnetite (Fe3O4) nanoparticles as a recyclable catalyst. With this greener method, the desired viny
