Literature DB >> 19555094

Preparation of pentafluorosulfanyl (SF5) pyrrole carboxylic acid esters.

William R Dolbier1, Zhaoyun Zheng.   

Abstract

Pyrrole derivatives bearing a pentafluorosulfanyl group are currently unknown. In this paper, a facile preparation of SF5-substituted pyrrole carboxylic acid esters in good yield is reported. Utilizing the cycloaddition of an azomethine ylide to pentafluorosulfanylalkynes, a series of dihydropyrroles were prepared and oxidized to the respective 1-tert-butyl-4-(pentafluorosulfanyl)pyrrole-2-carboxylic acid esters in good yield. Further treatment of these pyrroles with catalytic triflic acid allowed removal of the tert-butyl group.

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Year:  2009        PMID： 19555094     DOI： 10.1021/jo9007699

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


  4 in total

1.  Discovery of practical production processes for arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides): Beginning of a new era of "super-trifluoromethyl" arene chemistry and its industry.

Authors:  Teruo Umemoto; Lloyd M Garrick; Norimichi Saito
Journal:  Beilstein J Org Chem       Date:  2012-03-29       Impact factor: 2.883

2.  Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes.

Authors:  George Iakobson; Junyi Du; Alexandra M Z Slawin; Petr Beier
Journal:  Beilstein J Org Chem       Date:  2015-08-26       Impact factor: 2.883

3.  Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes.

Authors:  Norbert Vida; Jiří Václavík; Petr Beier
Journal:  Beilstein J Org Chem       Date:  2016-01-20       Impact factor: 2.883

4.  Synthesis of cis-C-iodo-N-tosyl-aziridines using diiodomethyllithium: reaction optimization, product scope and stability, and a protocol for selection of stationary phase for chromatography.

Authors:  Tom Boultwood; Dominic P Affron; Aaron D Trowbridge; James A Bull
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354
  4 in total

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