125951-09-9Relevant 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.
Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts
Dong, Jun,Xu, Jiaxi
, p. 2407 - 2415 (2018/04/16)
A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert -butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.
Decarbonylation of Salicylaldehyde Activated by p-Cymene Ruthenium(II) Dimer: Implication for Catalytic Alkyne Hydrothiolation
Modem, Sarangapani,Kankala, Shravankumar,Balaboina, Ramesh,Thirukovela, Narasimha Swamy,Jonnalagadda, Sreekantha B.,Vadde, Ravinder,Vasam, Chandra Sekhar
, p. 4635 - 4642 (2016/09/28)
A stoichiometric C–H activation/decarbonylation of salicylaldehyde by [(η6-p-cymene)RuCl2]2gave a carbonyl derivative [(η6-p-cymene)RuCl(CO)(Ph-O)] (1) without the use of CO gas. A variety of polar phosphines were then incorporated into compound 1 to give new RuIIcationic catalysts, [(η6-p-cymene)Ru(CO)(Ph-O)L]BF4(2–8). These were used to catalyse the hydrothiolation of alkynes with a range of thiols in aqueous THF to give anti-Markovnikov E-linear vinyl sulfides in high yields.
