54088-93-6Relevant articles and documents
B2cat2-Mediated Reduction of Sulfoxides to Sulfides
Takahashi, Fumiya,Nogi, Keisuke,Yorimitsu, Hideki
supporting information, p. 3009 - 3012 (2020/03/25)
An efficient and operationally simple method for the reduction of sulfoxides to sulfides has been developed using bis(catecholato)diboron (B2cat2) as a reducing agent. The present method accommodates various functional groups which are generally prone to reduction: halides, alkynes, carbonyls, nitriles, and heterocycles are totally intact, and only sulfoxide moieties undergo reduction chemoselectively. Moreover, the remaining diboron and the resulting boron-containing wastes are readily removable, the practicality of this protocol being thus demonstrated.
Aryldithiocarbamates as thiol alternatives in Cu-catalyzed C(aryl)-S coupling reactions using aryldiazonium tetrafluoroborate salts
Dutta, Soumya,Saha, Amit
, p. 9360 - 9366 (2019/11/13)
An efficient method for the synthesis of unsymmetrical diaryl sulfides has been developed by the C-S cross coupling of aryldithiocarbamates and aryldiazonium salts in the presence of CuI-2,2′-bipyridine and Zn. Aryldithiocarbamate compounds have been used here as thiol substitutes. The protocol shows wide substrate scope and good yields of the products.
Nickel Phosphite/Phosphine-Catalyzed C-S Cross-Coupling of Aryl Chlorides and Thiols
Jones, Kieran D.,Power, Dennis J.,Bierer, Donald,Gericke, Kersten M.,Stewart, Scott G.
supporting information, p. 208 - 211 (2018/01/17)
A method for the coupling of aryl chlorides and thiophenols using an air-stable nickel(0) catalyst is described. This thioetherification procedure can be effectively applied to a range of electronically diverse aryl/heteroaryl chlorides without more expensive metal catalysts such as palladium, iridium, or ruthenium. This investigation also illustrates both, a variety of thiol coupling partners and, in certain cases, the use of Cs2CO3.
AROMATIC SULFIDE COMPOUNDS AND METHODS AND USE THEREOF
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Paragraph 0168; 0173, (2015/11/03)
Described herein, inter alia, are aromatic sulfide compositions and methods for treating or preventing cancer using the same.
An efficient protocol for the carbon-sulfur cross-coupling of sulfenyl chlorides with arylboronic acids using a palladium catalyst
Gogoi, Prasanta,Kalita, Mukul,Barman, Pranjit
, p. 866 - 870 (2014/04/03)
An efficient protocol for carbon-sulfur bond formation is developed, which involves the cross-coupling of sulfenyl chlorides and arylboronic acids catalyzed by a novel palladium-Schiff base complex. Good to high product yields, short reaction times, and mild reaction conditions are important features of this new method. Georg Thieme Verlag Stuttgart · New York.
Diaryl and heteroaryl sulfides: Synthesis via sulfenyl chlorides and evaluation as selective anti-breast-cancer agents
Yonova, Ivelina M.,Osborne, Charlotte A.,Morrissette, Naomi S.,Jarvo, Elizabeth R.
, p. 1947 - 1953 (2014/04/03)
A mild protocol for the synthesis of diaryl and heteroaryl sulfides is described. In a one-pot procedure, thiols are converted to sulfenyl chlorides and reacted with arylzinc reagents. This method tolerates functional groups including aryl fluorides and chlorides, ketones, as well as N-heterocycles including pyrimidines, imidazoles, tetrazoles, and oxadiazoles. Two compounds synthesized by this method exhibited selective activity against the MCF-7 breast cancer cell line in the micromolar range.
Carbon-sulfur bond formation catalyzed by [Pd(IPr*OMe) (cin)Cl] (cin = cinnamyl)
Bastug, Gulluzar,Nolan, Steven P.
supporting information, p. 9303 - 9308 (2013/10/08)
The newly prepared complex [Pd(IPr*OMe)(cin)(Cl)] provides high catalytic activity for carbon-sulfur cross-coupling reactions. Nonactivated and deactivated aryl halides were successfully coupled with a large variety of aryl- and alkylthiols using this well-defined palladium N-heterocyclic carbene (NHC) complex.
Potassium isopropoxide: For sulfination it is the only base you need!
Sayah, Mahmoud,Organ, Michael G.
supporting information, p. 16196 - 16199 (2013/12/04)
PEPPSI max: KOiPr has been identified as the key ingredient for Pd-catalyzed sulfination (see scheme). Potassium is essential to keep the thiol concentration low, and isopropoxide is necessary for precatalyst activation and to break up Pd-sufide-based resting states. Together with the reactive Pd-PEPPSI-IPentCl o-picoline catalyst, this system couples profoundly deactivated partners at RT that other catalysts cannot accomplish in refluxing toluene. Copyright
Sulfination by using Pd-PEPPSI complexes: Studies into precatalyst activation, cationic and solvent effects and the role of butoxide base
Sayah, Mahmoud,Lough, Alan J.,Organ, Michael G.
, p. 2749 - 2756 (2013/03/14)
The activation of PEPPSI precatalysts has been systematically studied in Pd-catalysed sulfination. Under the reactions conditions of the sulfide and KOtBu in toluene, the first thing that happens is exchange of the two chlorides on the PEPPSI precatalyst with the corresponding sulfides, creating the first resting state; it is via this complex that all Pd enters the catalytic cycle. However, it is also from this same complex that a tri-Pd complex forms, which is a more persistent resting state. Under standard reaction conditions, this complex is catalytically inactive. However, if additional pyridine or a smaller base (i.e., KOEt) is added, this complex is broken down, presumably initially back to the first resting state and it is again capable of entering the catalytic cycle and completing the sulfination. Of note, once the tri-Pd complex forms, one equivalent of Pd is lost to the transformation. Related to this, the nature of the cation of the sulfide salt and solvent dielectric is very important to the success of this transformation. That is, the less soluble the salt the better the performance, which can be attributed to lowering sulfide concentration to avoid the movement of the Pd-NHC complex into the above described off-cycle sulfinated resting states.
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.
