Benzyl thioether formation merging copper catalysis

Abstract

A novel copper-catalyzed thioetherification reaction has been developed to afford benzyl thioethers in moderate to excellent yields.

Polyoxometalate-based ionic liquids: efficient reversible phase transformation-type catalysts for thiolation of alcohols to construct C–S bonds

“…According to the above results of control experiments and the previous research, 30,34 a possible carbocation intermediate involved mechanism for the thiolation of alcohols is proposed here (Scheme 5). Initially, the presence of the acidic catalyst was very important for the reaction (Table 1, entry 1) and the interaction A between the proton of the POM-ILs-SO 3 H and the hydroxyl of the alcohols was beneficial for the formation of intermediate B .…”

“…[19][20][21][22] At present, the preparation of thioethers by the reaction of sulfur-containing organic compounds with alcohols is mainly using Brønsted acids, 23 or using Lewis acids and transition metals as catalysts, such as metal triflates (AgOTf, Ga(OTf ) 3 , In(OTf ) 3 , Cu(OTf ) 2 ), ZnI 2 , silica gel supported ZrCl 4 , etc. [24][25][26][27][28][29][30][31] However, most of the above catalysts were difficult to recycle and separate with the target product. Some supported catalysts could be recycled, but the catalytic activity was relatively poor due to their small specific surface area.…”

Copper-Catalyzed Direct Thiolation of Ketones Using Sulfonohydrazides: A Synthetic Route to Benzylic Thioethers

“…Thioether synthesis typically includes the cross-coupling of thiols with aryl/alkyl halides under transition-metal catalysis; however, it is more feasible to use less expensive metals such as iron, copper, cobalt, nickel, and manganese . These techniques were used to synthesize a variety of sulfide compounds, but they suffer from some drawbacks. For example, they frequently call for harsh or extremely acidic conditions to encourage the interaction of alkyl alcohols with thioalcohols or thiophenols.…”