Literature DB >> 12443085

A mild, nonbasic synthesis of thioethers. The copper-catalyzed coupling of boronic acids with N-thio(alkyl, aryl, heteroaryl)imides.

Cecile Savarin1, Jiri Srogl, Lanny S Liebeskind.   

Abstract

[reaction: see text] A new synthesis of thioethers is described. The reaction of boronic acids with aryl, heteroaryl, and alkyl N-thioimides in the presence of catalytic quantities of a Cu(I) carboxylate affords good to excellent yields of thioethers. This reaction takes place in the absence of a base under mild conditions (THF, 45-50 degrees C, 2.5-12 h) and represents an interesting complement to known methods for thioether synthesis.

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Year:  2002        PMID: 12443085     DOI: 10.1021/ol026948a

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


  7 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Copper Mediated Coupling of 2-(Piperazine)-pyrimidine Iodides with Aryl Thiols using Cu(I)Thiophene-2-carboxylate.

Authors:  Liza Shrestha; Hardik J Patel; Yanlong Kang; Sahil Sharma; Gabriela Chiosis; Tony Taldone
Journal:  Tetrahedron Lett       Date:  2017-10-23       Impact factor: 2.415

3.  Synthesis of Copper(I) Thiolate Complexes in the Thioetherification of Aryl Halides.

Authors:  Chaohuang Chen; Zhiqiang Weng; John F Hartwig
Journal:  Organometallics       Date:  2012-10-04       Impact factor: 3.876

4.  Resting state and elementary steps of the coupling of aryl halides with thiols catalyzed by alkylbisphosphine complexes of palladium.

Authors:  Elsa Alvaro; John F Hartwig
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

5.  N-substituted imines by the copper-catalyzed N-imination of boronic acids and organostannanes with O-acyl ketoximes.

Authors:  Songbai Liu; Ying Yu; Lanny S Liebeskind
Journal:  Org Lett       Date:  2007-04-20       Impact factor: 6.005

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.  Environmentally benign approach towards C-S cross-coupling reaction by organo-copper(II) complex.

Authors:  Rabindranath Singha; Sailesh Chettri; Dhiraj Brahman; Biswajit Sinha; Pranab Ghosh
Journal:  Mol Divers       Date:  2021-01-03       Impact factor: 2.943

  7 in total

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