Literature DB >> 18611035

Stereo- and regiospecific cu-catalyzed cross-coupling reaction of vinyl iodides and thiols: a very mild and general route for the synthesis of vinyl sulfides.

M Shahjahan Kabir1, Michael L Van Linn, Aaron Monte, James M Cook.   

Abstract

A mild and efficient method for the copper-catalyzed formation of vinylic carbon-sulfur bonds has been developed. The desired vinyl sulfides are obtained in good to excellent yields, with full retention of stereochemistry. This method is particularly noteworthy given its mild reaction conditions, simplicity, and generality, as well as low cost of the catalyst system.

Entities:  

Year:  2008        PMID: 18611035     DOI: 10.1021/ol801149n

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


  8 in total

1.  Enantiospecific total synthesis of the important biogenetic intermediates along the ajmaline pathway, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epivellosimine and macusine A.

Authors:  Wenyuan Yin; M Shahjahan Kabir; Zhijian Wang; Sundari K Rallapalli; Jun Ma; James M Cook
Journal:  J Org Chem       Date:  2010-05-21       Impact factor: 4.354

2.  Radical-mediated thiodesulfonylation of the vinyl sulfones: Access to (α-fluoro)vinyl sulfides.

Authors:  Pablo R Sacasa; Jessica Zayas; Stanislaw F Wnuk
Journal:  Tetrahedron Lett       Date:  2009-09-23       Impact factor: 2.415

3.  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

4.  First application of an efficient and versatile ligand for copper-catalyzed cross-coupling reactions of vinyl halides with N-heterocycles and phenols.

Authors:  M Shahjahan Kabir; Michael Lorenz; Ojas A Namjoshi; James M Cook
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

5.  TBAI-assisted direct C-H activation of indoles with β-E-styrene sulfonyl hydrazides: a stereoselective access to 3-styryl thioindoles.

Authors:  Saira Hafeez; Aamer Saeed
Journal:  RSC Adv       Date:  2021-04-27       Impact factor: 4.036

Review 6.  Transition metal catalyzed synthesis of aryl sulfides.

Authors:  Chad C Eichman; James P Stambuli
Journal:  Molecules       Date:  2011-01-17       Impact factor: 4.411

7.  Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers.

Authors:  Davide Bello; David O'Hagan
Journal:  Beilstein J Org Chem       Date:  2015-10-14       Impact factor: 2.883

8.  New classes of Gram-positive selective antibacterials: inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis.

Authors:  M Shahjahan Kabir; Kathleen Engelbrecht; Rebecca Polanowski; Sarah M Krueger; Rachel Ignasiak; Marc Rott; William R Schwan; Mary E Stemper; Kurt D Reed; David Sherman; James M Cook; Aaron Monte
Journal:  Bioorg Med Chem Lett       Date:  2008-09-26       Impact factor: 2.823

  8 in total

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