Process for preparation of aryl thioethers and aryl selenoethers by copper(I) catalyzed coupling of thiols and selenols with aryl halides.

Title

Process for preparation of aryl thioethers and aryl selenoethers by copper(I) catalyzed coupling of thiols and selenols with aryl halides.

Subject

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Description

A mild, palladium-free improved process for prepn. of aryl thioethers and selenoethers comprise reaction of thiols and selenols with aryl halides, preferably aryl iodides catalyzed by copper(I) halide complexes with bidentate ligands, preferably with substituted phenanthrolines in an inert org. solvent such as toluene in a presence of a base, preferably potassium phosphate, cesium carbonate, sodium tert-butoxide; vinyl halides undergo coupling with thiols and selenols as well. In an example, 1-methyl-4-phenylthiobenzene was prepd. by coupling of 2.2 mmol of benzenethiol with 2.00 mmol of 1-iodo-4-methylbenzene in 6 mL of toluene in the presence of 3 mmol of NaOtBu, 10 mol% of CuI and 10 mol% of 2,9-dimethyl-1,10-phenanthroline (neocuproin) at 110° for 24 h with 94% yield. A variety of vinyl/aryl sulfides and vinyl/aryl selenides can be synthesized in excellent yields from readily available iodides and thiols or selenols. [on SciFinder(R)]

Creator

Venkataraman, Dhandapani; Bates, Craig G.; Gujadhur, Rattan K.

Source

U.S.

Date

2006

Rights

Application: US

Relation

Substitution reaction (arom.; process for prepn. of arom. and vinyl thioethers and selenoethers by copper(I)-catalyzed coupling of aryl and vinyl halides with thiols and selenols); Thioethers Role: SPN (Synthetic preparation), PREP (Preparation) (aryl; process for prepn. of arom. and vinyl thioethers and selenoethers by copper(I)-catalyzed coupling of aryl and vinyl halides with thiols and selenols); Ligands Role: CAT (Catalyst use), USES (Uses) (bidentate, phenanthrolines; process for prepn. of arom. and vinyl thioethers and selenoethers by copper(I)-catalyzed coupling of aryl and vinyl halides with thiols and selenols); Vinyl compounds Role: RCT (Reactant), RACT (Reactant or reagent) (halo; process for prepn. of arom. and vinyl thioethers and selenoethers by copper(I)-catalyzed coupling of aryl and vinyl halides with thiols and selenols); Coupling reaction catalysts (process for prepn. of arom. and vinyl thioethers and selenoethers by copper(I)-catalyzed coupling of aryl and vinyl halides with thiols and selenols); Aryl halides; Thiols Role: RCT (Reactant), RACT (Reactant or reagent) (process for prepn. of arom. and vinyl thioethers and selenoethers by copper(I)-catalyzed coupling of aryl and vinyl halides with thiols and selenols); Ethers Role: SPN (Synthetic preparation), PREP (Preparation) (selenoethers; process for prepn. of arom. and vinyl thioethers and selenoethers by copper(I)-catalyzed coupling of aryl and vinyl halides with thiols and selenols); Group VIA element compounds; Organic compounds Role: RCT (Reactant), RACT (Reactant or reagent) (selenols; process for prepn. of arom. and vinyl thioethers and selenoethers by copper(I)-catalyzed coupling of aryl and vinyl halides with thiols and selenols); Thioethers Role: SPN (Synthetic preparation), PREP (Preparation) (vinyl; process for prepn. of arom. and vinyl thioethers and selenoethers by copper(I)-catalyzed coupling of aryl and vinyl halides with thiols and selenols)

Language

written in English

Identifier

2004-889311