13963-35-4Relevant articles and documents
C-S bond formation catalyzed by N-heterocylic carbene palladium phosphine complexes
Fu, Ching-Feng,Liu, Yi-Hung,Peng, Shei-Ming,Liu, Shiuh-Tzung
, p. 2119 - 2122 (2010)
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.
Intermediates of copper(i)-catalyzed C-S cross coupling of thiophenol with aryl halide by in situ ESI-MS study
Cheng, Shao-Wen,Tseng, Mei-Chun,Lii, Kwang-Hwa,Lee, Chi-Rung,Shyu, Shin-Guang
, p. 5599 - 5601 (2011)
Complexes [Cu(SPh)2]-, [Cu(SPh)I]- and K[Cu(SPh)2(Ph)]+ were observed by in situ electrospray ionization mass spectrometry (ESI-MS) analysis of the copper(i)-catalyzed C-S coupling reaction under catalytic reaction conditions indicating that they are intermediates in the reaction. A catalytic cycle was proposed based on these observations.
A highly active and magnetically retrievable nanoferrite-DOPA-copper catalyst for the coupling of thiophenols with aryl halides
Baig, R. B. Nasir,Varma, Rajender S.
, p. 2582 - 2584 (2012)
Diaryl sulfides were synthesized using a magnetically recoverable heterogeneous Cu catalyst via one-pot multi component reaction using MW irradiation; the use of isopropanol as a benign reaction medium, easy recovery of the catalyst using an external magnet, efficient recycling, and the high stability of the catalyst render the protocol economic and sustainable. This journal is The Royal Society of Chemistry 2012.
Electrochemistry Enabled Nickel-Catalyzed Selective C?S Bond Coupling Reaction
Pan, Yi,Wang, Yang,Wang, Yi,Zhang, Feng
, (2022/02/16)
This work describes an electrochemical enabled nickel-catalyzed chemoselective C?S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C?S bond coupling has demonstrated excellent redox activity, scalability and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.
Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C?S/C?N Couplings
Martín, M. Trinidad,Marín, Mario,Maya, Celia,Prieto, Auxiliadora,Nicasio, M. Carmen
supporting information, p. 12320 - 12326 (2021/08/09)
Ni-catalyzed C?S cross-coupling reactions have received less attention compared with other C-heteroatom couplings. Most reported examples comprise the thioetherification of most reactive aryl iodides with aromatic thiols. The use of C?O electrophiles in this context is almost uncharted. Here, we describe that preformed Ni(II) precatalysts of the type NiCl(allyl)(PMe2Ar’) (Ar’=terphenyl group) efficiently couple a wide range of (hetero)aryl halides, including challenging aryl chlorides, with a variety of aromatic and aliphatic thiols. Aryl and alkenyl tosylates are also well tolerated, demonstrating, for the first time, to be competent electrophilic partners in Ni-catalyzed C?S bond formation. The chemoselective functionalization of the C?I bond in the presence of a C?Cl bond allows for designing site-selective tandem C?S/C?N couplings. The formation of the two C-heteroatom bonds takes place in a single operation and represents a rare example of dual electrophile/nucleophile chemoselective process.
Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters
Bie, Fusheng,Cao, Han,Liu, Chengwei,Liu, Xuejing,Shi, Yijun,Szostak, Michal,Zhou, Tongliang
, p. 8098 - 8103 (2021/10/25)
We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.
