Literature DB >> 16050711

Stereoselective hydrothiolation of alkynes catalyzed by cesium base: facile access to (Z)-1-alkenyl sulfides.

Azusa Kondoh1, Kazuaki Takami, Hideki Yorimitsu, Koichiro Oshima.   

Abstract

Treatment of alkyne with alkanethiol in the presence of a catalytic amount of cesium carbonate and a radical inhibitor in DMSO provides the corresponding adduct, (Z)-1-alkenyl alkyl sulfide, in good yield with high selectivity.

Entities:  

Year:  2005        PMID： 16050711     DOI： 10.1021/jo050931z

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  5 in total

1.  Hydrothiolation of benzyl mercaptan to arylacetylene: application to the synthesis of (E) and (Z)-isomers of ON 01910·Na (Rigosertib®), a phase III clinical stage anti-cancer agent.

Authors:  Venkat R Pallela; Muralidhar R Mallireddigari; Stephen C Cosenza; Balaiah Akula; D R C Venkata Subbaiah; E Premkumar Reddy; M V Ramana Reddy
Journal:  Org Biomol Chem       Date:  2013-02-06       Impact factor: 3.876

Review 2.  Metal Catalysis in Thiolation and Selenation Reactions of Alkynes Leading to Chalcogen-Substituted Alkenes and Dienes.

Authors:  Nikolai V Orlov
Journal:  ChemistryOpen       Date:  2015-09-09       Impact factor: 2.911

3.  Thiol-yne click reaction: an interesting way to derive thiol-provided catechols.

Authors:  Fabiana Nador; Juan Mancebo-Aracil; Duham Zanotto; Daniel Ruiz-Molina; Gabriel Radivoy
Journal:  RSC Adv       Date:  2021-01-07       Impact factor: 3.361

4.  Click Step-Growth Polymerization and E/Z Stereochemistry Using Nucleophilic Thiol-yne/-ene Reactions: Applying Old Concepts for Practical Sustainable (Bio)Materials.

Authors:  Joshua C Worch; Andrew P Dove
Journal:  Acc Chem Res       Date:  2022-08-25       Impact factor: 24.466

5.  Selectivity control in thiol-yne click reactions via visible light induced associative electron upconversion.

Authors:  Julia V Burykina; Nikita S Shlapakov; Evgeniy G Gordeev; Burkhard König; Valentine P Ananikov
Journal:  Chem Sci       Date:  2020-07-23       Impact factor: 9.825
  5 in total

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