Literature DB >> 19507847

Seleniranium ion-triggered reactions: new aspects of Friedel-Crafts and N-detosylative cyclizations.

Hwan Jung Lim1, T V RajanBabu.   

Abstract

Seleniranium ions at low temperatures (-90 to -78 degrees C) will initiate effective Friedel-Crafts cyclization if a suitably placed arene is allowed to react even when the arene is unactivated. These intermediates generated from N-aryl-N-tosylamides undergo a novel, surprisingly efficient, detosylative cyclization to form 5- or 6-membered nitrogen heterocycles. A debenzylation route is preferred if both benzyl and tosyl groups are present in the substrate.

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Year:  2009        PMID: 19507847      PMCID: PMC2742950          DOI: 10.1021/ol900961m

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


  7 in total

1.  Organoselenium Chemistry in Stereoselective Reactions.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-11-03       Impact factor: 15.336

2.  Selenocyclizations: control by coordination and by the counterion.

Authors:  Shaista S Khokhar; Thomas Wirth
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-01       Impact factor: 15.336

3.  Asymmetric carboselenenylation reaction of alkenes with aromatic compounds.

Authors:  Kazuki Okamoto; Yoshiaki Nishibayashi; Sakae Uemura; Akio Toshimitsu
Journal:  Angew Chem Int Ed Engl       Date:  2005-06-06       Impact factor: 15.336

4.  Lewis base activation of Lewis acids: development of a Lewis base catalyzed selenolactonization.

Authors:  Scott E Denmark; William R Collins
Journal:  Org Lett       Date:  2007-08-17       Impact factor: 6.005

Review 5.  Ag-mediated reactions: coupling and heterocyclization reactions.

Authors:  Jean-Marc Weibel; Aurélien Blanc; Patrick Pale
Journal:  Chem Rev       Date:  2008-07-11       Impact factor: 60.622

6.  Silver(I)-catalyzed facile synthesis of pyrazoles from propargyl N-sulfonylhydrazones.

Authors:  Young Tak Lee; Young Keun Chung
Journal:  J Org Chem       Date:  2008-05-20       Impact factor: 4.354

7.  Intramolecular arylation reactions of alkenes: a flexible approach to chromans and tetrahydroquinoline derivatives.

Authors:  José Barluenga; Mónica Trincado; Eduardo Rubio; José M González
Journal:  J Am Chem Soc       Date:  2004-03-24       Impact factor: 15.419

  7 in total
  3 in total

1.  Fe(OTf)3-catalysed Friedel-Crafts reaction of benzenoid arenes with α,β-unsaturated carbonyl compounds: easy access to 1,1-diarylalkanes.

Authors:  Aditya Bhattacharya; Pushpendra Mani Shukla; Biswajit Maji
Journal:  R Soc Open Sci       Date:  2017-10-25       Impact factor: 2.963

2.  Efficient Protocol for Synthesis of β-Hydroxy(alkoxy)selenides via Electrochemical Iodide-Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides.

Authors:  Jinyang Chen; Lan Mei; Haiying Wang; Li Hu; Xiaorui Sun; Jianwei Shi; Qiang Li
Journal:  ChemistryOpen       Date:  2019-09-10       Impact factor: 2.911

3.  Catalytic asymmetric tandem Friedel-Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans.

Authors:  Jiahuan Peng; Da-Ming Du
Journal:  Beilstein J Org Chem       Date:  2013-06-24       Impact factor: 2.883

  3 in total

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