33399-48-3Relevant articles and documents
Beyond the cyanine limit: Peierls distortion and symmetry collapse in a polymethine dye
Tolbert, Laren M.,Zhao, Xiaodong
, p. 3253 - 3258 (1997)
Theory predicts that cyanine dyes and related linear systems undergo symmetry collapse and bond localization at long chain lengths. Beyond this 'cyanine limit', the properties of these systems do not extrapolate from their shorter counterparts. To test this prediction, dipyridocyanines have been synthesized and shown to undergo such symmetry collapse with chain lengths as short as 13.
Deoxygenative C-S Bond Coupling with Sulfinates via Nickel/Photoredox Dual Catalysis
Deng, Guo-Jun,Huang, Huawen,Mao, Guojiang,Zhao, Feng,Zhong, Shuai,Zhou, Zhiwei
supporting information, p. 1865 - 1870 (2022/03/16)
The C-S bond formation from aryl halides and thiols has been well established under various catalytic systems. In this work, user-friendly sulfinates have been exploited as an efficient sulfenylating reagent in the C-S couplings through visible-light-induced photo/nickel dual catalysis under base- and external reductant-free conditions. A large number of aryl sulfide products were accessed with high selectivity and high tolerance of various functionalities.
Synthesis of Aryl Sulfides by Metal-Free Arylation of Thiols with Diaryliodonium Salts under Basic Conditions**
Kalek, Marcin,Rajkiewicz, Adam A.,Sarkar, Sudeep,Wojciechowska, Natalia
, (2022/02/07)
Metal-free arylation of thiols with diaryliodonium salts has been developed. The application of a strong organic base enables the C?S bond formation under mild and experimentally simple conditions. The method allows for the synthesis of aryl sulfides containing a broad range of aryl groups from an array of thiols, including aryl, heteroaryl, and alkyl ones. The mechanism of the reaction was studied by DFT calculations, demonstrating that it proceeds via the inner sphere pathway involving formation of an Ar2I(SR) intermediate, followed by reductive elimination.
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.
Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds
Lam, Long Yin,Ma, Cong
supporting information, p. 6164 - 6168 (2021/08/16)
A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.
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.
Surfactant-Type Catalyst for Aerobic Oxidative Coupling of Hydrazine with Thiol in Water
Ren, Xuanhe,Tang, Shanyu,Li, Longjia,Li, Jiao,Liang, Helong,Li, Ganzhong,Yang, Guanyu,Li, Heng,Yuan, Bingxin
, p. 8683 - 8690 (2019/07/08)
A series of PEG-functionalized nitrogen ligands were developed to conduct an aerobic oxidative cross-coupling reaction between alkyl- or aryl-hydrazines with thiols in water. This surfactant-type catalyst enables high efficiencies and selectivities, while tolerating a large variety of functional groups. The mother liquor is still catalytically active after five runs.
Synthesis and antifungal activities of pyridine bioisosteres of a bismuth heterocycle derived from diphenyl sulfone
Hafizur Rahman,Murafuji, Toshihiro,Yamashita, Kazuki,Narita, Masahiro,Miyakawa, Isamu,Mikata, Yuji,Ishiguro, Katsuya,Kamijo, Shin
, p. 1037 - 1052 (2018/08/28)
– Heterocyclic iodobismuthanes 7–9 [IBi(C6H4-2-SO2C5H3N-1′-)] derived from phenyl pyridinyl sulfones were synthesized. Their antifungal activities against the yeast Saccharomyces cerevisiae were compared with those of halobismuthanes [XBi(RC6H3-2-SO2C6H4-1′-)] (1: X=Cl; 2: X=I, R=H) derived from diphenyl sulfone derivatives to determine how the bioisosteric replacement of the benzene ring in 2 with the pyridine ring in 7–9 affects their activities. The antifungal activities of 7–9 were higher or comparable to those of 1 and 2. The DFT calculations suggested that the generation of the antifungal activity of the bismuthanes was well understood by the nucleophilic addition of methanethiolate anion as a model biomolecule at the bismuth atom to give an intermediate ate complex.
Palladium- and Nickel-Catalyzed Decarbonylative C-S Coupling to Convert Thioesters to Thioethers
Ichiishi, Naoko,Malapit, Christian A.,Wo?niak, Aukasz,Sanford, Melanie S.
supporting information, p. 44 - 47 (2018/01/17)
This Letter describes the development of a catalytic decarbonylative C-S coupling reaction that transforms thioesters into thioethers. Both Pd- and Ni-based catalysts are developed and applied to the construction of diaryl, aryl alkyl, and heterocycle-containing thioethers.
Iron(0) nanoparticles mediated direct conversion of aryl/heteroaryl amines to chalcogenides via in situ diazotization
Panja, Subir,Maity, Pintu,Kundu, Debasish,Ranu, Brindaban C.
supporting information, p. 3441 - 3445 (2017/08/10)
A simple procedure for the synthesis of organo-chalcogenides has been developed by the reaction of aryl/heteroaryl amines with di-aryl/heteroaryl dichalcogenides in the presence of tBuONO and Fe(0) nanoparticles. The reaction proceeds via in situ diazotization followed by chalcogenation. A series of functionalized diaryl/aryl heteroaryl/diheteroaryl/aryl-alkyl selenides, sulfides and tellurides have been obtained by this procedure. Significantly, using this procedure 2,4-dinitroaniline is converted to (2,4-dinitrophenyl)(phenyl)selane which is known as thioredoxin reductase (TR) and glutathione reductase (GR) inhibitor. The reaction goes by a radical pathway and a plausible mechanism has been suggested.
