Thiophenol, copper salt

Benzenesulfonyl chloride, 4-methyl- [p-Tol-uenesulfonyl chloride], 55, 57, 59 Benzenethiol [Phenol, thio-], 55, 122 Benzenethiol, copper(I) salt [Thiophenol, copper(I) salt], 55, 123 Benzenethiol, lithium salt [Thiophenol, lithium salt], 55, 1 22 Benzoic acid, 2-amino- [Anthramlic acid], p bromination of, 55, 23... 

Thionyl chloride, 55, 27 Thiophenol, 58, 144 Thiophenol, copper(I) salt, 55, 123 Thiophenol, lithium salt, 55, 122 Toluene, 56,86,58,125 Toluene, p-bromo-, 56, 86 Toluene, 4-bromo-, 55,49 Toluene, p-chloro-, 56, 86 Toluene, a-cyclohexyhdene-, 56, 105 Toluene, a (2 hydroxycyclohexyhdene)-, 56,105... 

Copper (I) thiophenolate [1192-40-1] M 172.7, m ca 280°, pKj 6.62 (for PhS ). The Cu salt can be extracted from a thimble (Soxhlet) with boiling MeOH. It is a green-brown powder which gives a yellow-green soln in pyridine. Wash with EtOH and dry in a vacuum. It can be ppted from a pyridine soln by addition of H2O, collect ppte, wash with EtOH and dry in a vacuum. [Synthesis 662 1974, J Am Chem Soc 79 170 1957-, Chem Ber 90 425 1957.]... 

Arylboronic acids, (ArB(OH)2, react with thiols and copper(II) acetate to give the corresponding alkyl aryl sulfide. " Arylboronic acids also react with N-methylthiosuccinimide, with a copper catalyst, to give the aryl methyl sulfide. " " In the presence of a palladium catalyst, thiophenols react with diaryliodonium salts. 

Most mercaptides are not available as commercial products, since large-scale applications of these chemical compounds are quite limited (only mercaptides of tin and antimony are used industrially as thermal stabilizers for poly(vinyl chloride) [de Sousa et al., 2000 Qu L. et al., 2002]). However, these compounds can be synthesized in a very simple way. Owing to their low water solubility, mercaptides can precipitate by reacting thiols (or thiophenols) with aqueous solutions of the corresponding metal salts. In addition to the well-known mercaptides of mercury, lead, zinc, and copper, many others, such as mercaptides of silver, gold, platinum, palladium, iridium, nickel, iron, cobalt, antimony, bismuth, and cadmium, have been prepared. 

In 2011 a copper-catalyzed thiolalion annulation reaction of 2-bromo alkynyl-benzenes 190 with sodinm sulfide has been developed. This approach provided 2-substituted benzo[fc]thiophenes in moderate to good yields [102], Also, synthesis of the 2-trifluoromethyl benzothiophene 192 was carried out in high yield using the thiophenol equivalent of the phenolic phosphonium bromide salt 191 [103],... 

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