A Facile One-pot Synthesis of Sulfides from Alkyl Halides and Alcohols Using Tetramethylthiourea

Abstract

Sulfides can be readily prepared under mild conditions by a reaction of tetramethylthiourea with alkyl halides and alcohols in the presence of sodium hydride in satisfactory yields. The scope and limitation of this method are also presented.

Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols

“…Indeed, Kajigaeshi published a general one-pot two-step convergent strategy for preparation of thioethers from primary alcohols utilizing isothiouronium salts ( Scheme 1B ). 8 This work showcases 12 examples with moderate yields, but establishes precedence for using thiouronium salts. Proline-derived cyclic iminium salts were used in a similar work in an attempt to kinetically resolve secondary benzylic alcohols with mediocre results ( Scheme 1C ).…”

Palladium(II) Complexes of Homologated Ferrocene Phosphanylether and Thioether Ligands

“…Eventually, compound 4 was synthesized by using the method developed by Kajigaeshi and co‐workers based on the reactions between the in situ formed S ‐alkylisothiouronium salts and alcoholates. Thus, the reaction of [(Me 2 N) 2 SMe]I with 5 /NaH (Scheme ) afforded the protected phosphanyl thioether 4 in yields of 28 and 45 % when performed in N , N ‐dimethylformamide and acetonitrile, respectively.…”

Triazabicyclodecene: An Effective Isotope Exchange Catalyst in CDCl3.

“…the site of deuterium incorporation in the substrate was determined by 2 H NMR spectroscopy relative to CHCl 3 (7.27 ppm).…”

“…CDCl 3 was used as lock and CHCl 3 as internal standard (7.27 ppm). 2 H NMR spectral data were recorded at 46 MHz and chemical shifts are reported relative to CDCl 3 (7.27 ppm). HRMS analysis was performed in positive electrospray mode.…”