Literature DB >> 16706544

Catalyst-free conjugated addition of thiols to alpha,beta-unsaturated carbonyl compounds in water.

Gopal L Khatik1, Raj Kumar, Asit K Chakraborti.   

Abstract

[reaction: see text] Catalyst-free conjugate addition of thiols to alpha,beta-unsaturated carbonyl compounds in water is reported. beta-Sulfido carbonyl compounds were formed at room temperature, in short times and with excellent chemoselectivity. Competitive dithiane/dithiolane formation, transesterification, and ester cleavage were not observed. Water played a dual role in simultaneously activating the alpha,beta-unsaturated carbonyl compound and the thiol. This new methodology constitutes an easy, highly efficient, and green synthesis of beta-sulfido carbonyl compounds.

Entities:  

Year:  2006        PMID: 16706544     DOI: 10.1021/ol060846t

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  12 in total

1.  Conjugate addition/cyclization sequence enables selective and simultaneous fluorescence detection of cysteine and homocysteine.

Authors:  Xiaofeng Yang; Yixing Guo; Robert M Strongin
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-20       Impact factor: 15.336

2.  Reversible Inter- and Intra-Microgel Cross-Linking using Disulfides.

Authors:  Jeffrey C Gaulding; Michael H Smith; John S Hyatt; Alberto Fernandez-Nieves; L Andrew Lyon
Journal:  Macromolecules       Date:  2012-01-01       Impact factor: 5.985

3.  Thiol-activated DNA damage by α-bromo-2-cyclopentenone.

Authors:  Mostafa I Fekry; Nathan E Price; Hong Zang; Chaofeng Huang; Michael Harmata; Paul Brown; J Scott Daniels; Kent S Gates
Journal:  Chem Res Toxicol       Date:  2011-01-20       Impact factor: 3.739

4.  Organometallic Complex Formed by an Unconventional Radical S-Adenosylmethionine Enzyme.

Authors:  Min Dong; Masaki Horitani; Boris Dzikovski; Maria-Eirini Pandelia; Carsten Krebs; Jack H Freed; Brian M Hoffman; Hening Lin
Journal:  J Am Chem Soc       Date:  2016-08-02       Impact factor: 15.419

5.  Thiol-selective fluorogenic probes for labeling and release.

Authors:  Vu Hong; Alexander A Kislukhin; M G Finn
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

6.  A fast response highly selective probe for the detection of glutathione in human blood plasma.

Authors:  Yixing Guo; Xiaofeng Yang; Lovemore Hakuna; Aabha Barve; Jorge O Escobedo; Mark Lowry; Robert M Strongin
Journal:  Sensors (Basel)       Date:  2012-05-08       Impact factor: 3.576

7.  Immobilized TiO2 nanoparticles on carbon nanotubes: an efficient heterogeneous catalyst for the synthesis of chromeno[b]pyridine derivatives under ultrasonic irradiation.

Authors:  Shahrzad Abdolmohammadi; Behrooz Mirza; Esmail Vessally
Journal:  RSC Adv       Date:  2019-12-17       Impact factor: 4.036

8.  Antiparallel Dynamic Covalent Chemistries.

Authors:  Bartosz M Matysiak; Piotr Nowak; Ivica Cvrtila; Charalampos G Pappas; Bin Liu; Dávid Komáromy; Sijbren Otto
Journal:  J Am Chem Soc       Date:  2017-05-09       Impact factor: 15.419

9.  Tetrabutylammonium bromide media aza-Michael addition of 1,2,3,6-tetrahydrophthalimide to symmetrical fumaric esters and acrylic esters under solvent-free conditions.

Authors:  Gholamhassan Imanzadeh; Farzaneh Ahmadi; Mohammadreza Zamanloo; Yagoub Mansoori
Journal:  Molecules       Date:  2010-10-21       Impact factor: 4.411

10.  An efficient heterogeneous catalyst (CuO@ARF) for on-water C-S coupling reaction: an application to the synthesis of phenothiazine structural scaffold.

Authors:  Debasish Sengupta; Basudeb Basu
Journal:  Org Med Chem Lett       Date:  2014-12-29
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