19654-17-2Relevant academic research and scientific papers
Facile synthesis of 2-(substitutedbenzylsulfanyl)-benzothiazoles and their antimicrobial activity screening
Kumar, Ramanatham Vinod,Kumar, Kotha V. S. R. Seshu,Gopal, Kotarkonda Raja
, p. 153 - 156 (2005)
A simple and convenient procedure for the preparation of 2-(substitutedbenzylsulfanyl)benzothiazoles by the reaction of 2-mercaptobenzothiazole and benzyl bromides in acetone/K2CO 3 has been reported and the compounds have been scree
Conformational Analysis of Acyclic α-Fluoro Sulfur Motifs
Erdeljac, Nathalie,Mück-Lichtenfeld, Christian,Daniliuc, Constantin G.,Gilmour, Ryan
, p. 13704 - 13715 (2020)
Bioactive small molecules containing α-fluoro sulfur motifs [RS(O)nCH2F] are appearing with increasing frequency in the pharmaceutical and agrochemical sectors. Prominent examples include the anti-asthma drug Flovent and t
Preparation of alkyl aryl sulfides from alcohols and 2- sulfanylbenzothiazole by a new type of oxidation-reduction condensation using aryl diphenylphosphinite and benzoquinone derivatives
Kuroda, Kiichi,Heyashi, Yujiro,Mukaiyama, Teruaki
, p. 592 - 593 (2008)
A method for the preparation of alkyl aryl sulfides from alcohols and 2-sulfanylbenzothiazole by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite and 2.6-dimethoxy-1,4-benzoquinone is described. In this reaction, the chiral alcohols are converted into the corresponding chiral sulfides with almost complete inversion of configurations under mild and neutral conditions. Copyright
Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions
Fang, Jing,Li, Ting,Ma, Xiang,Sun, Jiuchang,Cai, Lei,Chen, Qi,Liao, Zhiwen,Meng, Lingkui,Zeng, Jing,Wan, Qian
, p. 288 - 292 (2021/07/25)
A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.
Ag-Cu copromoted direct C2-H bond thiolation of azoles with Bunte salts as sulfur sources
Du, Xiao,Hu, Yuntao,Wang, Rui,Wei, Yingsu,Xu, Hongyan,Zhang, Ying,Zhao, Huaiqing
supporting information, p. 5899 - 5904 (2021/07/12)
A direct C2-H thiolation of azoles with Bunte salts was achieved under the combined action of copper and silver salts. This protocol could furnish various substituted 2-thioazoles in moderate to good yields. This method has a broad substrate scope and shows good functional group tolerance.
Unusual Deoxidative Coupling Reaction of β-Sulfinyl Esters with Benzylic Trimethylammonium Salts
Chen, Feng,Feng, Hang,He, Ze,Zeng, Qingle,Zhang, Qiaoling
, p. 7806 - 7812 (2021/06/25)
A KOH-promoted unusual deoxidative coupling reaction of β-sulfinyl esters with benzylic trimethylammonium salts to produce thioethers is discovered for the first time. If quaternary ammonium salts synthesized from enantiomerically enriched amines are adopted, highly enantiomerically enriched benzyl thioethers (>95-99% ee) with configurations opposite to those of the enantiomerically enriched amines are obtained.
Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides
Li, Fuhai,Wang, Dan,Chen, Hongyi,He, Ze,Zhou, Lihong,Zeng, Qingle
, p. 13029 - 13032 (2020/11/07)
A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. This journal is
One-Pot Substitution of Aliphatic Alcohols Mediated by Sulfuryl Fluoride
Dubois, Rudy,Epifanov, Maxim,Hodgson, Jack W.,Mo, Jia Yi,Sammis, Glenn M.
supporting information, p. 4958 - 4962 (2020/04/22)
The Mitsunobu reaction is a powerful transformation for the one-pot activation and substitution of aliphatic alcohols. Significant efforts have focused on modifying the classic conditions to overcome problems associated with purification from phosphine-based byproducts. Herein, we report a phosphine free method for alcohol activation and substitution that is mediated by sulfuryl fluoride. This new method is effective for a wide range of primary alcohols using phthalimide, di-tert-butyl-iminodicarboxylate, and aromatic thiol nucleophiles in 74 % average yield. Activated carbon nucleophiles and a deactivated phenol were also effective for this reaction in good yields. Secondary alcohols were also successful substrates using aryl thiols, affording the corresponding sulfides in 56 % average yield with enantiomeric ratios up to 99:1. This new protocol has a distinct synthetic advantage over many existing phosphine-based methods as the byproducts are readily separable. This feature was exploited in several examples that did not require chromatography for purification. Furthermore, the mild reaction conditions enabled further in situ derivatization for the one-pot conversion of alcohols to amines or sulfones. This method also provides a boarder nucleophile scope compared to existing phosphine-free methods.
Three-Component Synthesis of 2-Substituted Thiobenzoazoles Using Tetramethyl Thiuram Monosulfide (TMTM) as Thiocarbonyl Surrogate
Wang, Xi,Wu, Chun-Yan,Li, Yue-Sheng,Dong, Zhi-Bing
, p. 6770 - 6775 (2020/11/23)
A metal-free synthesis of 2-benzyl/allyl-substituted thiobenzoazoles was developed starting from tetramethyl thiuram monosulfide (TMTM) which served as thiocarbonyl surrogate. By using 2-aminophenols (or 2-aminothiophenols, or 1,2-phenylenediamines) and TMTM as starting materials, 2-mercaptobenzoazoles could be synthesized efficiently. The subsequent C–S bond formation with benzyl/allyl halides gave the final products (2-benzyl/allyl-substituted thiobenzoazoles) with good to excellent yields. The metal-free conditions, inexpensive and easily available starting materials, and broad substrate scope are the advantageous features of this protocol.
Selective C-H chalcogenation of thiazoles: Via thiazol-2-yl-phosphonium salts
Zi, You,Wagner, Konrad,Sch?mberg, Fritz,Vilotijevic, Ivan
, p. 5183 - 5191 (2020/07/23)
Thiazoles and benzothiazoles undergo regioselective C2-H chalcogenation via the sequence of thiazole C2-functionalization with phosphines to produce phosphonium salts which in turn react with S- and Se-centered nucleophiles to give products of C2-H chalco
