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.

Download full-text PDF

Source
http://dx.doi.org/10.1039/c8ob01855cDOI Listing

Publication Analysis

Top Keywords

iodine-catalyzed cross-coupling
4
cross-coupling isocyanides
4
isocyanides thiols
4
thiols synthesis
4
synthesis s-thiocarbamates
4
s-thiocarbamates novel
4
novel efficient
4
efficient metal
4
metal free
4
free redox-neutral
4

Similar Publications

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 PDF

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 PDF

An Efficient Approach for 3,3-Disubstituted Oxindoles Synthesis: Aryl Iodine Catalyzed Intramolecular C-N Bond Oxidative Cross-Coupling.

Org 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 PDF

Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions.

J 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 PDF

Iodine-catalyzed cross-coupling of isocyanides and thiols for the synthesis of S-thiocarbamates.

Org 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.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!