4074-62-8Relevant academic research and scientific papers
C-S cross-coupling reactions catalyzed by a non-symmetric phosphinito-thiophosphinito PSCOP-Ni(II) pincer complex
Serrano-Becerra, Juan M.,Valdés, Hugo,Canseco-González, Daniel,Gómez-Benítez, Valente,Hernández-Ortega, Simón,Morales-Morales, David
, p. 3377 - 3380 (2018)
A new non-symmetric phosphinito-thiophosphinito POCSP-Ni(II) pincer compound was synthetized and characterized. The molecular structure of [NiCl{C6H3-2-(OPPh2)-6-(SPPh2)}] (1) was unequivocally determined by single crystal X-ray diffraction analysis, showing the Ni center to be located into a slightly distorted square planar geometry. This compound was used as efficient catalyst in C-S couplings of disulfides with iodobenzenes, exhibiting good activity and selectivity as well as tolerance to different functional groups.
Mono- And Dinuclear α-Diimine Nickel(II) and Palladium(II) Complexes in C-S Cross-Coupling
Talukder, Md Muktadir,Miller, Justin T.,Cue, John Michael O.,Udamulle, Chinthaka M.,Bhadran, Abhi,Biewer, Michael C.,Stefan, Mihaela C.
, p. 83 - 94 (2021/01/14)
The usefulness of transition metal catalytic systems in C-S cross-coupling reactions is significantly reduced by air and moisture sensitivity, as well as harsh reaction conditions. Herein, we report four highly air- and moisture-stable well-defined mononuclear and bridged dinuclear α-diimine Ni(II) and Pd(II) complexes for C-S cross-coupling. Various ligand frameworks, including acenaphthene- and iminopyridine-based ligands, were employed, and the resulting steric properties of the catalysts were evaluated and correlated with reaction outcomes. Under aerobic conditions and low temperatures, both Ni and Pd systems exhibited broader substrate scope and functional group tolerance than previously reported catalysts. Over 40 compounds were synthesized from thiols containing alkyl, benzyl, and heteroaryl groups. Also, pharmaceutically active heteroaryl moieties are incorporated from thiol and halide sources. Notably, the bridged dinuclear five-coordinate Ni complex has outperformed the remaining three mono four- or six-coordinate complexes by giving almost quantitative yields across a broad substrate scope.
Bismuth(III)-Promoted Acetylation of Thioethers into Thioacetates
Jevric, Martyn,Petersen, Anne Ugleholdt,Mans?, Mads,Madsen, Anders,Nielsen, Mogens Br?ndsted
, p. 4675 - 4688 (2015/08/03)
The thioacetate group is extensively employed as an anchoring group for attachment of molecules onto gold surfaces or between electrodes in molecular electronics. On account of its ready hydrolysis, it is often incorporated in the last step of a synthetic
Palladium-mediated strategies for functionalizing the dihydroazulene photoswitch: Paving the way for its exploitation in molecular electronics
Jevric, Martyn,Broman, Soren Lindbaek,Nielsen, Mogens Brondsted
, p. 4348 - 4356 (2013/06/05)
The dihydroazulene (DHA)/vinylheptafulvene (VHF) photo/thermoswitch has attracted interest as a molecular switch for advanced materials and molecular electronics. We report here two synthetic approaches using palladium catalysis for synthesizing dihydroazulene (DHA) photoswitches with thioacetate anchoring groups intended for molecular electronics applications. The first methodology involves a Suzuki coupling using tert-butyl thioether protecting groups. Conversion to the thioacetate using boron tribromide/acetyl chloride results in the formation of the product as a mixture of regioisomers mediated by a ring-opening reaction. The second approach circumvents isomerization by the synthesis of stannanes as intermediates and their use in a Stille coupling. Although fully unsaturated azulenes are formed as byproducts during the synthesis of the DHA stannanes, this approach allowed the regioselective incorporation of the thioacetate anchoring group in either one of the two ends (positions 2 or 7) or at both.
Copper-free sonogashira coupling reaction using a trans-spanning 1,2-Bis(2-thienylethynyl)benzene ligand
Atobe, Shingo,Sonoda, Motohiro,Suzuki, Yuki,Shinohara, Hiroyuki,Yamamoto, Takuya,Ogawa, Akiya
supporting information; experimental part, p. 980 - 982 (2012/02/01)
Novel copper-free Sonogashira coupling reaction of aryl halides with terminal acetylenes proceeded in the presence of 1,2-bis(2-thienylethynyl) benzene (1) as a trans-bidentatable ligand.
A very active Cu-catalytic system for the synthesis of aryl, heteroaryl, and vinyl sulfides
Kabir, M. Shahjahan,Lorenz, Michael,Van Linn, Michael L.,Namjoshi, Ojas A.,Ara, Shamim,Cook, James M.
experimental part, p. 3626 - 3643 (2010/07/14)
Figure presented cis-1,2-Cyclohexanediol (L3) has been shown to be an efficient and versatile bidentate O-donor ligand that provides a highly active Cu-catalytic system. It was more effective than diols such as trans-1,2-cyclohexanediol or ethylene glycol. This commercially available cis-1,2-cyclohexanediol ligand facilitated the Cu-catalyzed cross-coupling reactions of alkyl, aryl, or heterocyclic thiols with either alkyl, aryl, heterocyclic, or substituted vinyl halides. This new catalytic system promoted the mild and efficient stereo- and regiospecific synthesis of biologically important vinyl sulfides. The yields obtained using electron-rich substituted vinyl sulfides with this catalyst system are generally 75-98%. Most importantly, this singular catalyst system is extremely versatile and provides entry into a wide range of sulfides. This method is particularly noteworthy given its mild reaction conditions, simplicity, generality, and exceptional level of functional group tolerance.
Zinc-mediated palladium-catalyzed formation of carbon-sulfur bonds
Eichman, Chad C.,Stambuli, James P.
supporting information; experimental part, p. 4005 - 4008 (2009/10/02)
(Chemical Equation Presented) A catalytic amount of zinc chloride in combination with a palladium catalyst ligated by a monodentate phosphine allows the coupling of aryl and alkyl thiols with aryl bromides in high yields. The addition of zinc chloride to a palladium catalyst system that reportedly failed to promote sulfide formation allows this once ineffective catalyst system to provide the sulfide product in good yield. This paper describes a high-yielding and general monodentate phosphine-ligated palladium catalyst for biaryl and alkyl aryl sulfide formation.
Iron-catalyzed thioetherification of thiols with aryl iodides
Wu, Jhih-Ru,Lin, Che-Hung,Lee, Chin-Fa
supporting information; experimental part, p. 4450 - 4452 (2009/12/29)
FeCl3 in combination with bisphosphine ligands represents an efficient catalyst system for the cross-coupling of aryl- and alkyl thiols with aryl iodides, a broad spectrum of functional groups can be tolerated during the catalysis. The Royal Society of Chemistry 2009.
1-[β(R-thio)phenethyl]imidazoles and derivatives thereof
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, (2008/06/13)
Novel 1-[β-(R-thio)phenethyl]-imidazoles and the corresponding 1-[β-(R-sulfinyl)phenethyl]imidazoles and 1-[β-(R-sulfonyl)phenethyl]imidazoles wherein R is alkyl, alkenyl, aralkenyl, substituted aralkenyl, alkynyl, cycloalkyl, cycloalkyl alkyl, aralkyl, substituted aralkyl, aryl or substituted aryl; and the antimicrobial acid addition salts thereof, are useful as antifungal, anti-bacterial and anti-protozoal agents.
