16704-47-5Relevant articles and documents
Safe, Scalable, Inexpensive, and Mild Nickel-Catalyzed Migita-Like C?S Cross-Couplings in Recyclable Water
Yu, Tzu-Yu,Pang, Haobo,Cao, Yilin,Gallou, Fabrice,Lipshutz, Bruce H.
supporting information, p. 3708 - 3713 (2020/12/17)
A new approach to C?S couplings is reported that relies on nickel catalysis under mild conditions, enabled by micellar catalysis in recyclable water as the reaction medium. The protocol tolerates a wide range of heteroaromatic halides and thiols, including alkyl and heteroaryl thiols, leading to a variety of thioethers in good isolated yields. The method is scalable, results in low residual metal in the products, and is applicable to syntheses of targets in the pharmaceutical area. The procedure also features an associated low E Factor, suggesting a far more attractive entry than is otherwise currently available, especially those based on unsustainable loadings of Pd catalysts.
A Robust Pd-Catalyzed C-S Cross-Coupling Process Enabled by Ball-Milling
Browne, Duncan L.,Jones, Andrew C.,Nicholson, William I.,Smallman, Harry R.
, p. 7433 - 7438 (2020/10/09)
An operationally simple mechanochemical C-S coupling of aryl halides with thiols has been developed. The reaction process operates under benchtop conditions without the requirement for a (dry) solvent, an inert atmosphere, or catalyst preactivation. The reaction is finished within 3 h. The reaction is demonstrated across a broad range of substrates; the inclusion of zinc metal has been found to be critical in some instances, especially for coupling of alkyl thiols.
Metal-free C-H thioarylation of arenes using sulfoxides: A direct, general diaryl sulfide synthesis
Fernández-Salas, José A.,Pulis, Alexander P.,Procter, David J.
, p. 12364 - 12367 (2016/10/22)
Metal-free C-H thioarylation of arenes and heteroarenes using methyl sulfoxides constitutes a general protocol for the synthesis of high value diaryl sulfides. The coupling of arenes and heteroarenes with in situ activated sulfoxides is regioselective, uses readily available starting materials, is operationally simple, and tolerates a wide range of functional groups.
Synthesis of Aryl Sulfides: Metal-Free C-H Sulfenylation of Electron-Rich Arenes
Hostier, Thomas,Ferey, Vincent,Ricci, Gino,Gomez Pardo, Domingo,Cossy, Janine
, p. 3898 - 3901 (2015/08/18)
A simple, efficient, and practical metal-free C-H sulfenylation of substituted electron-rich arenes has been developed. This method is highly regioselective, and the corresponding aryl sulfides were obtained in moderate to excellent yields from stable and
Palladium catalyzed aryl(alkyl)thiolation of unactivated arenes
Saravanan, Perumal,Anbarasan, Pazhamalai
, p. 848 - 851 (2014/03/21)
A general palladium-catalyzed aryl(alkyl)thiolation of various substituted unactivated arenes is accomplished for the synthesis of diverse unsymmetrical diaryl(alkyl) sulfides in good yield employing electrophilic sulfur reagent 6 derived from succinimide. The developed strategy was coupled with intramolecular arylation of a C-H bond to afford dibenzothiphene derivatives, an important moiety in material science as organic semiconductors.
A new family of nucleophiles for photoinduced, copper-catalyzed cross-couplings via single-electron transfer: Reactions of thiols with aryl halides under mild conditions (O C)
Uyeda, Christopher,Tan, Yichen,Fu, Gregory C.,Peters, Jonas C.
supporting information, p. 9548 - 9552 (2013/07/19)
Building on the known photophysical properties of well-defined copper-carbazolide complexes, we have recently described photoinduced, copper-catalyzed N-arylations and N-alkylations of carbazoles. Until now, there have been no examples of the use of other families of heteroatom nucleophiles in such photoinduced processes. Herein, we report a versatile photoinduced, copper-catalyzed method for coupling aryl thiols with aryl halides, wherein a single set of reaction conditions, using inexpensive CuI as a precatalyst without the need for an added ligand, is effective for a wide range of coupling partners. As far as we are aware, copper-catalyzed C-S cross-couplings at 0 C have not previously been achieved, which renders our observation of efficient reaction of an unactivated aryl iodide at -40 C especially striking. Mechanistic investigations are consistent with these photoinduced C-S cross-couplings following a SET/radical pathway for C-X bond cleavage (via a Cu(I)-thiolate), which contrasts with nonphotoinduced, copper-catalyzed processes wherein a concerted mechanism is believed to occur.
Silver catalyzed C-C and C-S coupling of aryl halides and thiols with boronic acids
Das, Rima,Chakraborty, Debashis
, p. 7023 - 7027 (2013/01/15)
An efficient Ag(I) catalyzed carbon-carbon and carbon-sulfur bond formation reaction of aryl halides and thiols with boronic acids has been demonstrated. Using this protocol, substrates with a wide range of functional group including electron-rich, and electron deficient substituents have been explored. These reactions are particularly useful to prepare symmetrical and unsymmetrical biphenyls and thioethers. These products were isolated in high yield.
Bi(III)-catalyzed C-S cross-coupling reaction
Malik, Payal,Chakraborty, Debashis
, p. 557 - 561 (2013/01/15)
A direct synthetic route for the C-S coupling of aryl halides with thiophenols is described. This method is tolerant to electron-withdrawing and electron-donating functional groups and also to the presence of functional groups in the ortho position of the aryl iodide or thiophenol. Aryl iodides are coupled with thiophenols without affecting the other functionalities present in the aryl ring. These reactions follow second-order kinetics. Copyright
Indium-catalyzed C-S cross-coupling of aryl halides with thiols
Reddy, V. Prakash,Swapna,Kumar, A. Vijay,Rao, K. Rama
supporting information; experimental part, p. 3189 - 3191 (2009/08/08)
Indium-catalyzed C-S cross-coupling of aromatic and alkane thiols with aryl halides proceeds smoothly in the presence of In(OTf)3 (10 mol %), TMEDA (20 mol %), and KOH as a base in DMSO at 135 °C. When this protocol was utilized, a variety of thiols could be cross-coupled with aryl halides to afford the corresponding aryl sulfides in good to excellent yields.
CuO nanoparticles catalyzed C-N, C-O, and C-S cross-coupling reactions: Scope and mechanism
Jammi, Suribabu,Sakthivel, Sekarpandi,Rout, Laxmidhar,Mukherjee, Tathagata,Mandai, Santu,Mitra, Raja,Saha, Prasenjit,Punniyamurthy, Tharmalingam
experimental part, p. 1971 - 1976 (2009/07/01)
CuO nanoparticles have been studied for C-N, C-O, and C-S bond formations via cross-coupling reactions of nitrogen, oxygen, and sulfur nucleophiles with aryl halides. Amides, amines, imidazoles, phenols, alcohols and thiols undergo reactions with aryl iodides in the presence of a base such as KOH, Cs 2CO3, and K2CO3 at moderate temperature. The procedure is simple, general, ligand-free, and efficient to afford the cross-coupled products in high yield.
