14965-37-8Relevant articles and documents
Formation of meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols from cyclohexane-1,3-diones
Do Van Thanh, Nhan,Patra, Subrata,Clive, Derrick L.J.
, p. 4343 - 4350 (2018/07/13)
Reaction of cyclohexane-1,3-diones with TsCl/Et3N and treatment of the resulting 3-(tosyloxy)cyclohex-2-en-1-ones with aryl- or alkyl thiols and K2CO3 in MeCN gives 3-(arylsulfanyl)cyclohex-2-en-1-ones or 3-(alkylsulfanyl)cyclohex-2-en-1-ones, respectively. These compounds are easily brominated at C-2 by using NBS in MeCN; exposure to DBU in MeCN at room temperature then causes aromatization to afford meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols.
A general, efficient, and functional-group-tolerant catalyst system for the palladium-catalyzed thioetherification of aryl bromides and iodides
Fernandez-Rodriguez, Manuel A.,Hartwig, John F.
experimental part, p. 1664 - 1672 (2009/07/17)
The cross-coupling reaction of aryl bromides and iodides with aliphatic and aromatic thiols catalyzed by palladium complexes of the bisphosphine ligand CyPF-tBu (1) is reported. Reactions occur in excellent yields, broad scope, high tolerance of functional groups, and with turnover numbers that exceed those of previous catalysts by 2 or 3 orders of magnitude. These couplings of bromo- and iodoarenes are more efficient than the corresponding reactions of chloroarenes and could be conducted with less catalyst loading and/or milder reaction conditions. Consequently, limitations regarding scope and functional group tolerance previously reported in the coupling of aryl chlorides are now overcome.
