One‐Pot Copper‐Catalysed Thioetherification of Aryl Halides Using Alcohols and Lawesson's Reagent in Diglyme

Abstract

A new protocol for the thioetherification of structurally varied alcohols with aryl halides using Lawesson's reagent, catalysed by copper(I) iodide, and using diglyme as a safe solvent was developed. Using this method, the reactions of aryl halides proceeded efficiently, and the desired sulfides were obtained in high to excellent yields. The method uses alcohols

Copper-Catalyzed Three-Component Coupling Reaction of Aryl Iodides, a Disilathiane, and Alkyl Benzoates Leading to a One-Pot Synthesis of Alkyl Aryl Sulfides

“…7 Other reports have described the palladium-catalyzed coupling of iodobenzenes, sodium thiosulfate (Na 2 S 2 O 3 ), and alkyl halides, and also the use of copper-catalyzed nitrobenzenes, sodium thiosulfate (Na 2 S 2 O 3 ) and alkyl halides, with both approaches leading to the production of alkyl aryl sulfides. 8 Additionally, sulfur sources, such as thiourea, 9 carbon disulfide (CS 2 ), 10 elemental sulfur (S 8 ), 11 and Lawesson's reagent, 12 behave as a suitable sulfur source for this type of coupling protocol, leading to alkyl aryl sulfides.…”

Synthesis of Functionalized Arenopyrans and Arenylsulfanes by Reacting Nitroallylic Acetates with Arenols and Arenethiols

“…Thioethers are also excellent ligands in co‐ordination chemistry . Allyl aryl thioethers, in particular, are synthesized through electrophilic substitution of allylsilanes, transition metal catalyzed coupling reactions, reaction of arenethiol with allylic acetate/carbonate, allylic halide, allylic alcohol and allene, reaction of aryl halide with allyl thiol, and other miscellaneous methods such as decarbonylative C‐S coupling of thioethers, dechalcogenative rearrangement of disulfides etc.…”

Decyanative Cross‐Coupling of Cyanopyrimidines with O‐, S‐, and N‐Nucleophiles: A Route to Alkoxylpyrimidines, Aminopyrimidines and Alkylthiopyrimidines

“…2‐(Dodecylthio)pyrimidine (10d): Yield 95 % (213 mg); yellow oil; IR (KBr) ν̃: 3852, 3749, 3648, 3444, 3031, 2956, 2926, 2855, 1566, 1383, 1205, 774, 630 cm –1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (ppm): 8.50 (d, J = 4.8 Hz, 2H), 6.93 (t, J = 4.8 Hz, 1H), 3.14 (t, J = 7.4 Hz, 2H), 1.78–1.68 (m, 2H), 1.48–1.43 (m, 2H), 1.29–1.28 (m, 8H), 0.90–0.86 (m, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ (ppm):172.8, 157.1, 116.2, 31.8, 30.8, 29.1, 29.0, 28.9, 22.6, 14.0; ESI‐MS: m/z 225.10 [M + H] + .…”