A novel and efficient metal free, redox-neutral method for the synthesis of secondary thiocarbamates by cross-coupling of readily available thiophenol and isocyanides has been developed. The present methodology exhibits a broad substrate scope with good to excellent yields without an additive/extra oxidant under mild reaction conditions catalyzed by inexpensive iodine as the catalyst.
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http://dx.doi.org/10.1039/c8ob01855c | DOI Listing |
Chem Commun (Camb)
June 2023
Department of Chemistry, University of Calcutta, 92 APC Road, Kolkata-700009, India.
Our study describes a new development featuring iodine-catalyzed two consecutive oxidative cross-coupling reactions involving C(sp)-H of benzyl amines followed by intramolecular cyclization in water under air. Here, C-N coupling followed by C-C coupling occurs in a green environment to provide a variety of 5-pyrazino[2,3-]indoles within a short time period.
View Article and Find Full Text PDFJ Org Chem
June 2022
Department of Chemistry, Indian Institute of Technology Madras, Chennai600 036, Tamil Nadu, India.
An iodine-catalyzed denitrative C-S cross-coupling reaction has been developed to attain thiochromanones from 2'-nitrochalcones and xanthate. The strategy was extended for a three-component synthesis of thiochromenes via intermolecular C-S cross-coupling followed by aldol reaction. The reaction proceeds via activation of the keto group of chalcone through a halogen bond complex with iodine/denitrative C-S bond formation with xanthate/sulfa-Michael addition to chalcones.
View Article and Find Full Text PDFOrg Lett
November 2021
Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Institute of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.
Herein, we report the first intramolecular C-N bond formation of phenylpropanamide derivatives via organocatalytic oxidative reactions, affording 3,3-disubstituted oxindole derivatives with up to 99% yield. The high efficiency of this reaction is exemplified by the transition metal-free mild conditions and the ability to perform the reaction on a gram scale. Meanwhile, the DFT calculation of the catalytic oxidative transformation pathway has also been studied.
View Article and Find Full Text PDFJ Org Chem
March 2019
Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials , Nanjing Tech University, Nanjing 211816 , China.
An efficient method for the synthesis of alkyl indium reagent by means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good compatibility to a variety of sensitive functional groups. By replacing THF with DMA and using 0.
View Article and Find Full Text PDFOrg Biomol Chem
September 2018
School of Chemical Sciences and Pharmacy, Central University of Rajasthan, NH8, Bandarsindri, Ajmer-305817, Rajasthan, India.
A novel and efficient metal free, redox-neutral method for the synthesis of secondary thiocarbamates by cross-coupling of readily available thiophenol and isocyanides has been developed. The present methodology exhibits a broad substrate scope with good to excellent yields without an additive/extra oxidant under mild reaction conditions catalyzed by inexpensive iodine as the catalyst.
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