59010-83-2Relevant academic research and scientific papers
Site-Selective Synthesis of Aryl Sulfides via Oxidative Aromatization of Cyclohexanones with Thiophenols
Xiao, Fuhong,Tang, Minli,Huang, Huawen,Deng, Guo-Jun
, p. 512 - 523 (2021/12/27)
We have introduced a metal-free facile access for the thiolation/aromatization of cyclohexanones with thiophenols to the corresponding aryl sulfides. The dehydroaromatic reaction of non-aromatic cyclohexanones proceeded smoothly using oxygen as a green oxidant.
Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides
Zhang, Weigang,Huang, Mengjun,Zou, Zhenlei,Wu, Zhengguang,Ni, Shengyang,Kong, Lingyu,Zheng, Youxuan,Wang, Yi,Pan, Yi
, p. 2509 - 2514 (2021/03/01)
Redox-active benzimidazolium sulfonamides as thiolating reagents have been developed for reductive C-S bond coupling. The IMDN-SO2R reagent provides a bench-stable cationic precursor to generate a portfolio of highly active N-S intermediates, which can be successfully applied in cross-electrophilic coupling with various organic halides. The employment of an electrophilic sulfur source solved the problem of catalyst deactivation and avoided odorous thiols, featuring practical conditions, broad substrate scope, and excellent tolerance.
Phenyldithiocarbamates: Efficient Sulfuration Reagents in the Chan–Lam Coupling Reaction
Cheng, Yu,Liu, Xing,Dong, Zhi-Bing
, p. 815 - 820 (2018/02/21)
The Chan–Lam coupling reaction starting from phenyldithiocarbamates and phenylboronic acids is reported. To avoid using the volatile, hazardous, and foul-smelling thiols, which are sometimes expensive and not sufficiently available, phenyldithiocarbamates can be employed. They are demonstrated to be good sulfuration reagents in the Chan–Lam coupling to prepare biaryl sulfides. By using this protocol, dithiocarbamate substrates with a wide range of functional groups including electron-rich and electron-deficient ones are explored to obtain the desired substituted biaryl sulfides smoothly. This method is ligand-free, has a broad substrate scope, enables good yields, and is easy to perform. It provides a facile and convenient preparation of biaryl sulfides.
Rh(III)-Catalyzed Direct ortho-Chalcogenation of Phenols and Anilines
Yang, Shiping,Feng, Boya,Yang, Yudong
, p. 12430 - 12438 (2017/12/08)
A highly efficient Rh(III)-catalyzed direct C-H chalcogenation of phenols and anilines has been achieved with the assistance of the 2-pyridyl group. The reaction features a broad substrate scope, good functional group tolerance, complete monothiolation selectivity, and easily removable directing group.
Nickel-Catalyzed C–S Coupling: Synthesis of Diaryl Sulfides Starting from Phenyldithiocarbamates and Iodobenzenes
Liu, Xing,Cao, Qiang,Xu, Wan,Zeng, Meng-Tian,Dong, Zhi-Bing
, p. 5795 - 5799 (2017/10/23)
A nickel-catalyzed C–S bond-formation protocol for the synthesis of diaryl sulfides is described. In a reaction catalyzed by NiCl2, phenyldithiocarbamates react with iodobenzenes to give diaryl sulfides smoothly in good to excellent yields (66–93 %). The catalyst is cheap, the reaction is easy to carry out, the substrate scope is broad, and the yields are good. Thus, this gives an alternative way to prepare diaryl sulfides.
Aryne 1,2,3-Trifunctionalization with Aryl Allyl Sulfoxides
Li, Yuanyuan,Qiu, Dachuan,Gu, Rongrong,Wang, Junli,Shi, Jiarong,Li, Yang
supporting information, p. 10814 - 10817 (2016/09/12)
An aryne 1,2,3-trisubstitution with aryl allyl sulfoxides is accomplished, featuring an incorporation of C-S, C-O, and C-C bonds on the consecutive positions of a benzene ring. The reaction condition is mild with broad substrate scope. Preliminary mechani
A mild and facile synthesis of aryl and alkenyl sulfides via copper-catalyzed deborylthiolation of organoborons with thiosulfonates
Yoshida, Suguru,Sugimura, Yasuyuki,Hazama, Yuki,Nishiyama, Yoshitake,Yano, Takahisa,Shimizu, Shigeomi,Hosoya, Takamitsu
, p. 16613 - 16616 (2015/11/25)
An efficient deborylthiolation of aryl- and alkenylborons with thiosulfonates has been achieved under mild conditions using a copper catalyst. All steps of the experimental process were free from unpleasant odors. The mild reaction conditions as well as ready availability of boron compounds and thiosulfonates enabled easy access to an array of sulfides, including those bearing sensitive functional groups.
Generation of arynes triggered by sulfoxidemetal exchange reaction of ortho-sulfinylaryl triflates
Yoshida, Suguru,Uchida, Keisuke,Hosoya, Takamitsu
supporting information, p. 116 - 118 (2014/01/23)
Arynes were efficiently generated from readily available ortho-sulfinylaryl triflates by the treatment with phenylmagnesium bromide in tetrahydrofuran at 78 C. Aryne generation was initiated by a rapid sulfoxidemetal exchange reaction, followed by the immediate elimination of the ortho-OTf group. Various arynophiles efficiently reacted with arynes generated by this method within 10min, providing the corresponding adducts in high yields.
Iodine-promoted 2-arylsulfanylphenol formation using cyclohexanones as phenol source
Chen, Ya,Xiao, Fuhong,Chen, Hui,Liu, Saiwen,Deng, Guo-Jun
, p. 44621 - 44628 (2014/12/10)
A novel method for the formation of 2-arylsulfanylphenols using cyclohexanones as phenol source via dehydrogenation is described. Various aromatic sodium sulfinates and sulfonyl chlorides acted as efficient coupling partners to construct new C-S bonds in the presence of an iodine promoter.
Iodine-catalyzed efficient 2-arylsulfanylphenol formation from thiols and cyclohexanones
Liao, Yunfeng,Jiang, Pengcheng,Chen, Shanping,Qi, Hongrui,Deng, Guo-Jun
, p. 3302 - 3306 (2013/12/04)
A novel method for the formation of 2-arylsulfanylphenols from thiols and cyclohexanones is described. Iodine was used as an effective catalyst for this kind of transformation. Cyclohexanones were used as a phenol source via a dehydrogenation and tautomerization reaction.
