Literature DB >> 17288374

Convenient synthesis of unsymmetrical organochalcogenides using organoboronic acids with dichalcogenides via cleavage of the S-S, Se-Se, or Te-Te bond by a copper catalyst.

Nobukazu Taniguchi1.   

Abstract

This article describes the methodology for a copper-catalyzed preparation of numerous monochalcogenides from dichalcogenides with organoboronic acids. Unsymmetrical diorgano-monosulfides, selenides, and tellurides can be synthesized by the coupling of dichalcogenides with aryl- or alkylboronic acids using a copper catalyst in air. The present reaction can take advantage of both organochalcogenide groups on dichalcogenide.

Entities:  

Year:  2007        PMID: 17288374     DOI: 10.1021/jo062131+

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


  11 in total

Review 1.  Arylation Chemistry for Bioconjugation.

Authors:  Chi Zhang; Ekaterina V Vinogradova; Alexander M Spokoyny; Stephen L Buchwald; Bradley L Pentelute
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-15       Impact factor: 15.336

Review 2.  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

3.  Transition metal photoredox catalysis of radical thiol-ene reactions.

Authors:  Elizabeth L Tyson; Michael S Ament; Tehshik P Yoon
Journal:  J Org Chem       Date:  2012-11-12       Impact factor: 4.354

4.  Synthesis of high enantiopurity N-protected alpha-amino ketones by thiol ester-organostannane cross-coupling using pH-neutral conditions.

Authors:  Hao Li; Hao Yang; Lanny S Liebeskind
Journal:  Org Lett       Date:  2008-08-30       Impact factor: 6.005

5.  Nano copper oxide catalyzed synthesis of symmetrical diaryl sulfides under ligand free conditions.

Authors:  K Harsha Vardhan Reddy; V Prakash Reddy; A Ashwan Kumar; G Kranthi; Yvd Nageswar
Journal:  Beilstein J Org Chem       Date:  2011-06-30       Impact factor: 2.883

6.  Copper-Catalyzed Synthesis of Unsymmetrical Diorganyl Chalcogenides (Te/Se/S) from Boronic Acids under Solvent-Free Conditions.

Authors:  Sumbal Saba; Giancarlo Vaccari Botteselle; Marcelo Godoi; Tiago Elias Allievi Frizon; Fábio Zazyki Galetto; Jamal Rafique; Antonio L Braga
Journal:  Molecules       Date:  2017-08-18       Impact factor: 4.411

Review 7.  Transition metal catalyzed synthesis of aryl sulfides.

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

8.  An Umpolung Approach for the Chemoselective Arylation of Selenocysteine in Unprotected Peptides.

Authors:  Daniel T Cohen; Chi Zhang; Bradley L Pentelute; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-07-30       Impact factor: 15.419

9.  Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides.

Authors:  Yohsuke Kobiki; Shin-Ichi Kawaguchi; Takashi Ohe; Akiya Ogawa
Journal:  Beilstein J Org Chem       Date:  2013-06-13       Impact factor: 2.883

10.  Synthesis and initial screening of lactate dehydrogenase inhibitor activity of 1,3-benzodioxole derivatives.

Authors:  Dicky Annas; Se-Yun Cheon; Mohammad Yusuf; Sung-Jin Bae; Ki-Tae Ha; Kang Hyun Park
Journal:  Sci Rep       Date:  2020-11-16       Impact factor: 4.379

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