26388-18-1Relevant academic research and scientific papers
Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds
Lam, Long Yin,Ma, Cong
supporting information, p. 6164 - 6168 (2021/08/16)
A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.
Achieving Nickel Catalyzed C-S Cross-Coupling under Mild Conditions Using Metal-Ligand Cooperativity
Sikari, Rina,Sinha, Suman,Das, Siuli,Saha, Anannya,Chakraborty, Gargi,Mondal, Rakesh,Paul, Nanda D.
, p. 4072 - 4085 (2019/04/01)
A simple and efficient approach of C-S cross-coupling of a wide variety of (hetero)aryl thiols and (hetero)aryl halides under mild conditions, mostly at room temperature, catalyzed by well-defined singlet diradical Ni(II) catalysts bearing redox noninnocent ligands is reported. Taking advantage of ligand centered redox events, the high-energetic Ni(0)/Ni(II) or Ni(I)/Ni(III) redox steps were avoided in the catalytic cycle. The cooperative participation of both nickel and the coordinated ligands during oxidative addition/reductive elimination steps allowed us to perform the catalytic reactions under mild conditions.
Microwave-Assisted Copper-Catalyzed Cross-Coupling Reaction of Thiols with Aryl Iodides in Water
Chen, Yi-An,Badsara, Satpal Singh,Tsai, Wan-Ting,Lee, Chin-Fa
, p. 181 - 186 (2015/05/04)
Microwave-promoted C-S bond formation from thiols and aryl iodides in the presence of a copper catalyst is reported. A combination of copper(II) oxide and 1,10-phenanthroline catalyzes this reaction. A variety of aryl iodides react smoothly with thiols to provide the corresponding aryl sulfides in good to excellent yields. Notably, the reactions proceed in water with a short reaction time (30 minutes). This system shows broad functional-group tolerance; amino, chloro, bromo, acetyl, and nitro groups are unaffected by the reaction conditions.
An efficient copper-catalyzed cross-coupling reaction of thiols with aryl iodides
Kao, Hsin-Lun,Chen, Chin-Keng,Wang, Yu-Jen,Lee, Chin-Fa
experimental part, p. 1776 - 1781 (2011/05/03)
Commercially available Cu2O powder is a very reactive catalyst for the coupling of thiols to aryl iodides. A variety of functional groups including esters, unprotected amines, alcohols, and heterocycles tolerate the reaction conditions. Moreover, di-ortho-substituted aryl iodides with sterically demanding substrates were also coupled to give the desired aryl thioethers in good to excellent yields. Copyright
Synthesis of CuO on mesoporous silica and its applications for coupling reactions of thiols with aryl iodides
Chen, Chin-Keng,Chen, Yan-Wun,Lin, Che-Hung,Lin, Hong-Ping,Lee, Chin-Fa
supporting information; experimental part, p. 282 - 284 (2010/05/01)
Novel CuO on mesoporous silica is prepared under a convenient approach, and has been shown to be an efficient catalyst for cross-coupling reactions of thiols with aryl iodides with only 1.0-5.0 mol% catalyst loading.
C-S bond formation catalyzed by N-heterocylic carbene palladium phosphine complexes
Fu, Ching-Feng,Liu, Yi-Hung,Peng, Shei-Ming,Liu, Shiuh-Tzung
experimental part, p. 2119 - 2122 (2010/04/26)
N-Heterocyclic carbenes (NHCs) are known to be useful ligands for palladium-complex catalysis. It was found that [(NHC)Pd(PPh3)Cl2] is an effective pre-catalyst in Pd-catalyzed C-S cross coupling reactions to produce the functionalized sulfides in excellent yields. The turn over frequency (TOF) for the coupling of p-CH3C6H4Br with p-CH3C6H4SH reaches to 6.25 (mol of product) (mole of catalyst)-1 h-1.
