Synthesis of sulfides (thioethers) and derivatives

Recent Literature

A new synthetic method for the preparation of potassium organotrifluoroborates through nucleophilic substitution of potassium bromo- and iodomethyltrifluoroborates is described. Potassium halomethyltrifluoroborates have been prepared via in situ reaction of n-BuLi with dibromo- and diiodomethane, respectively, in the presence of trialkyl borates, followed by treatment with KHF₂.
G. A. Molander, J. Ham, Org. Lett., 2006, 8, 2031-2034.

Epoxides can be opened under neutral conditions with alcohols and thiols in the presence of a catalytic amount of erbium(III) triflate, affording the corresponding β-alkoxy alcohols and β-hydroxy sulfides in high yields. In water, epoxide ring opening occurs to produce the corresponding diols in good yields.
R. Dalpozzo, M. Nardi, M. Oliverio, R. Paonessa, A. Procopio, Synthesis, 2009, 3433-3438.

Aziridines undergo an efficient, mild and regioselective ring opening with various thiols in the presence of 5 mol% bismuth triflate to afford the corresponding β-aminosulfides in excellent yields.
J. S. Yadav, B. V. S. Reddy, G. Baishya, P. V. Reddy, S. J. Harshavardhan, Synthesis, 2004, 1854-1858.

Sterically encumbered chiral pyrrolidine derivatives are highly efficient organocatalysts for the direct enantioselective α sulfenylation of aldehydes using an electrophilic sulfur source.
M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jorgensen, Angew. Chem. Int. Ed., 2005, 44, 794-797.

The anti-Markovnikov addition of thiols to alkenes using CeCl₃ as catalyst leads to products in very good yields. The reaction occurred under solvent-free conditions at room temperature.
C. C. Silveira, S. R. Mendes, F. M. Líbero, Synlett, 2010, 790-792.

A highly selective anti-Markovnikov addition of thiols to unactivated alkenes in water at room temperature without any additive is a very simple and efficient method for the synthesis of linear thioethers.
B. C. Ranu, T. Mandal, Synlett, 2007, 925-928.

A regio and anti-selective copper-catalyzed 1,2-hydroxysulfenylation of alkenes can be carried out by the use of disulfides and acetic acid. Reoxidation of intermediate sulfides by oxygen enables the use of both organosulfide groups of the disulfides.
N. Taniguchi, J. Org. Chem., 2006, 71, 7874-7876.

p-Toluenesulfonic acid efficiently catalyzes direct nucleophilic substitutions of the hydroxy groups of propargylic alcohols with a large variety of carbon- and heteroatom-centered nucleophiles. Reactions can be conducted under mild conditions and in air without the need for dried solvents.
R. Sanz, A. Martinez, J. M. Alvarez-Gutierrez, F. Rodriquez, Eur. J. Org. Chem., 2006, 1383-1386.