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One‐Pot Thioetherification of Aryl Halides Using Thiourea and Alkyl Bromides Catalyzed by Copper(I) Iodide Free from Foul‐Smelling Thiols in Wet Polyethylene Glycol (PEG 200)
Author(s) -
Firouzabadi Habib,
Iranpoor Nasser,
Gholinejad Mohammad
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900671
Subject(s) - chemistry , aryl , alkyl , iodide , thiourea , halide , polyethylene glycol , organic chemistry , peg ratio , polymer chemistry , potassium carbonate , iodine , catalysis , finance , economics
In this article, we have developed a new protocol for the thioarylation of structurally diverse alkyl bromides such as benzyl, cinnamyl, n ‐octyl, cyclohexyl, cyclopentyl, and tert ‐butyl bromides with aryl iodides, bromides and an activated chloride using thiourea catalyzed by copper(I) iodide in wet polyethylene glycol (PEG 200) as an eco‐friendly medium in the presence of potassium carbonate at 80 and 100 °C under an inert atmosphere. The process is free from foul‐smelling thiols which makes this method more practical for the thioetherification of aryl halides. Another important feature of this method is the variety of alkyl bromides which are commercially available for the in situ generation of thiolate ions with respect to the existing protocols in which the less commercially available thiols are directly used for the preparation of arylthio ethers.