13963-35-4Relevant academic research and scientific papers
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.
A SIMPLE PREPARATION OF SYMMETRICAL AND UNSYMMETRICAL DIARYL SULFIDES FROM ARENEDIAZONIUM TETRAFLUOROBORATES
Petrillo, Giovanni,Novi, Marino,Garbarino, Giacomo,Dell'Erba, Carlo
, p. 6365 - 6368 (1985)
The reaction between arenediazonium tetrafluoroborates and arenethiolates in Me2SO represents a mild, efficient and safe alternative to the Ziegler synthesis of diaryl sulfides.
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.
Calix[8]arene nanoreactor for Cu(i)-catalysed C-S coupling
Guzmán-Percástegui, Edmundo,Hernández, David J.,Castillo, Ivan
, p. 3111 - 3114 (2016)
The catalytic activity of Cu(i) confined within a phenanthroline-containing calix[8]arene derivative was tested in C-S cross-coupling reactions. The substrate selectivity, solvent dependence, and catalyst loading differ significantly from those reported for bimetallic molecular systems. The putative monomeric complex represents the first calix[8]arene functionalised for endo-oriented metal chelation used as a nanoreactor.
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.
AlCl3-mediated aromatic phenylthiation with N-phenylthiophthalimide
Suwa, Satoshi,Sakamoto, Takeshi,Kikugawa, Yasuo
, p. 980 - 982 (1999)
N-Phenylthiophthalimide reacts with AlCl3 or TiCl4 in arenes to give phenylthiated arenes alone via a phenylsulfenium ion intermediate, modified neglect of diatomic overlap (MNDO) molecular orbital calculations of which revealed that the positive charge preferentially populates the sulfur atom rather than the phenyl group in the phenylsulfenium ion.
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.
Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters
Cao, Han,Liu, Xuejing,Bie, Fusheng,Shi, Yijun,Han, Ying,Yan, Peng,Szostak, Michal,Liu, Chengwei
, p. 10829 - 10837 (2021/07/28)
Decarbonylative synthesis of thioethers from thioesters proceeds in the presence of a catalytic amount of [Rh(cod)Cl]2 (2 mol %). The protocol represents the first Rh-catalyzed decarbonylative thioetherification of thioesters to yield valuable thioethers. Notable features include the absence of phosphine ligands, inorganic bases, and other additives and excellent group tolerance to aryl chlorides and bromides that are problematic using other metals to promote decarbonylation. Gram scale synthesis, late-stage pharmaceutical derivatization, and orthogonal site-selective cross-couplings by C-S/C-Br cleavage are reported.
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.
A Visible-Light-Harvesting Covalent Organic Framework Bearing Single Nickel Sites as a Highly Efficient Sulfur–Carbon Cross-Coupling Dual Catalyst
Chen, Hui,Liu, Wanlu,Laemont, Andreas,Krishnaraj, Chidharth,Feng, Xiao,Rohman, Fadli,Meledina, Maria,Zhang, Qiqi,Van Deun, Rik,Leus, Karen,Van Der Voort, Pascal
supporting information, p. 10820 - 10827 (2021/04/09)
Covalent Organic Frameworks (COFs) have recently emerged as light-harvesting devices, as well as elegant heterogeneous catalysts. The combination of these two properties into a dual catalyst has not yet been explored. We report a new photosensitive triazine-based COF, decorated with single Ni sites to form a dual catalyst. This crystalline and highly porous catalyst shows excellent catalytic performance in the visible-light-driven catalytic sulfur–carbon cross-coupling reaction. Incorporation of single transition metal sites in a photosensitive COF scaffold with two-component synergistic catalyst in organic transformation is demonstrated for the first time.
