| Reference | 1. Org Biomol Chem. 2017 Feb 1;15(5):1254-1260. doi: 10.1039/c6ob02465c.<br />
Transition metal-free direct trifluoromethylthiolation of indoles using trifluoromethanesulfonyl chloride in the presence of triphenylphosphine.<br />
Lu K(1), Deng Z(2), Li M(1), Li T(2), Zhao X(2).<br />
Author information: (1)China International Science and Technology Cooperation Base of Food Nutrition/Safety and Medicinal Chemistry, Key Laboratory of Industrial Microbiology of Ministry of Education, Tianjin Key Laboratory of Industry Microbiology, College of Biotechnology, Tianjin University of Science & Technology, Tianjin, 300457, China. [email protected]. (2)College of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Key laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, Ministry of Education, Tianjin Normal University, Tianjin 300387, China. [email protected].<br />
A novel triphenylphosphine-mediated direct trifluoromethylthiolation of indole derivatives using trifluoromethanesulfonyl chloride as the SCF3 source was developed. Sodium iodide facilitated this transformation by generating iodine in situ which was found to accelerate this transformation. The use of a transition metal-free protocol, readily available reagents, and mild reaction conditions allowed this protocol to be easily scaled up.<br />
DOI: 10.1039/c6ob02465c PMID: 28098311<br />
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2. J Am Chem Soc. 2013 Jun 19;135(24):8782-5. doi: 10.1021/ja402455f. Epub 2013 Jun 11.<br />
Trifluoromethanesulfonyl hypervalent iodonium ylide for copper-catalyzed trifluoromethylthiolation of enamines, indoles, and β-keto esters.<br />
Yang YD(1), Azuma A, Tokunaga E, Yamasaki M, Shiro M, Shibata N.<br />
Author information: (1)Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.<br />
A novel electrophilic-type trifluoromethylthiolation reagent, a trifluoromethanesulfonyl hypervalent iodonium ylide, was designed and reacted well with various nucleophiles to afford the desired CF3S-substituted products. In situ reduction of the trifluoromethanesulfonyl group to give the trifluoromethylthio group, which is the key step in this process, was realized in the presence of copper(I) chloride.<br />
DOI: 10.1021/ja402455f PMID: 23738814 [Indexed for MEDLINE]<br />
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3. J Org Chem. 2020 Oct 2;85(19):12374-12381. doi: 10.1021/acs.joc.0c01634. Epub 2020 Sep 11.<br />
Synthesis of Thiocarbamoyl Fluorides and Isothiocyanates Using Amines with CF(3)SO(2)Cl.<br />
Wei J(1), Liang S(1), Jiang L(1), Yi W(1).<br />
Author information: (1)School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. China.<br />
A practical and efficient method to synthesize thiocarbamyl fluorides and isothiocyanates from amines with trifluoromethanesulfonyl chloride was developed. In the presence of the reducing agent triphenylphosphine and sodium iodide, thiocarbamyl fluorides and isothiocyanates were synthesized from secondary/primary amine in moderate to excellent yields, respectively. A broad scope of substrates and good functional group compatibility were observed.<br />
DOI: 10.1021/acs.joc.0c01634 PMID: 32866002<br />
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4. Org Lett. 2021 Jul 2;23(13):5102-5106. doi: 10.1021/acs.orglett.1c01642. Epub 2021 Jun 22.<br />
FeCl(2)-Mediated Regioselective Aminochlorination and Aminoazidation of Styrenes with Trifluoromethanesulfonyl Azide.<br />
Zhao J(1), Huang HG(1), Li W(1), Liu WB(1).<br />
Author information: (1)Sauvage Center for Molecular Sciences; Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education; College of Chemistry and Molecular Sciences, Wuhan University. 299 Bayi Road, Wuhan, Hubei 430072, China.<br />
An efficient aminochlorination reaction of stryenes is described using N3SO2CF3 as an amination reagent and FeCl2 as a chloride source. The operationally simple procedure features mild reaction conditions, good functional group compatibility, and high regioselectivity. An example of aminobromination using FeBr2 is also realized. Additionally, a one-pot aminoazidation of styrenes is achieved by adding sodium azide to the reaction. The gram-scale synthesis and downstream derivatization of the products are showcased as well.<br />
DOI: 10.1021/acs.orglett.1c01642 PMID: 34156853<br />
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5. ACS Omega. 2019 Oct 7;4(17):17230-17235. doi: 10.1021/acsomega.9b01724. eCollection 2019 Oct 22.<br />
Synthesis, Pharmacological and Toxicological Screening of Penicillin-Triazole Conjugates (PNTCs).<br />
Sahu A(1), Sahu P(2), Agrawal R(1).<br />
Author information: (1)Department of Pharmaceutical Sciences, Dr. Harisingh Gour Vishwavidyalaya, Sagar, Madhya Pradesh 470003, India. (2)Department of Chemistry, Central University of Kerala, Periye, Kerala 671320, India.<br />
A series of hybrid antimicrobial compounds were prepared by carboxylic acid protection of 6-aminopenicillanic acid using benzyl alcohol and thionyl chloride succeeded by azide displacement using trifluoromethanesulfonyl azide in dichloromethane. The azide thus formed was reacted with substituted alkynes to furnish benzyl-protected penicillin-triazole conjugates. Benzyl deprotection of the conjugates resulted in furnishing PNTCs under water methanol mixture using Pd/C as a catalyst. The PNTCs (7a-j) formed were screened for in vitro antibacterial potency against pathogenic strains of Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus pyogenes and antifungal potency against Candida albicans, Aspergillus niger, and Aspergillus clavatus. Further antimicrobial evaluation revealed compounds 7c, 7d, 7e, 7g, and 7i to be the most compounds of the series with minimum inhibitory concentration value for antibacterial in the range 0.5-50 μg/mL and for antifungal in the range 9-300 μg/mL. Toxicological analysis documented for compounds 7c, 7d, 7e, 7g, and 7i revealed compound 7i to be the most promising member of the series with 1000 and 500 mg/kg LD50, and no-observed-adverse-effect level to facilitate future clinical studies of the same.<br />
Copyright © 2019 American Chemical Society.<br />
DOI: 10.1021/acsomega.9b01724 PMCID: PMC6812114 PMID: 31656896<br />
Conflict of interest statement: The authors declare no competing financial interest.
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