Literature DB >> 16986964

Efficient C-N bond formations catalyzed by a proton-exchanged montmorillonite as a heterogeneous Brønsted acid.

Ken Motokura1, Nobuaki Nakagiri, Kohsuke Mori, Tomoo Mizugaki, Kohki Ebitani, Koichiro Jitsukawa, Kiyotomi Kaneda.   

Abstract

Nucleophilic addition of sulfonamides and n class="Chemical">carboxamides to simple alkenes proceeded smoothly using a proton-exchanged montmorillonite catalyst. The spent catalyst was recovered easily from the reaction mixture and was reusable at least five times without any loss of activity. The unique acidity of the proton-exchanged montmorillonite (H-mont) catalyst was found to be applicable to additional reactions: substitution of hydroxyl groups of alcohols with amides and anilines.

Entities:  

Year:  2006        PMID: 16986964     DOI: 10.1021/ol0619821

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


  6 in total

1.  Homogeneous catalytic hydroamination of alkynes and allenes with ammonia.

Authors:  Vincent Lavallo; Guido D Frey; Bruno Donnadieu; Michele Soleilhavoup; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Catalytic intermolecular hydroamination of vinyl ethers.

Authors:  Nirmal K Pahadi; Jon A Tunge
Journal:  Synlett       Date:  2009-12-01       Impact factor: 2.454

3.  Intramolecular "hydroiminiumation and -amidiniumation" of alkenes: a convenient, flexible, and scalable route to cyclic iminium and imidazolinium salts.

Authors:  Rodolphe Jazzar; Jean-Baptiste Bourg; Rian D Dewhurst; Bruno Donnadieu; Guy Bertrand
Journal:  J Org Chem       Date:  2007-04-05       Impact factor: 4.354

4.  Intramolecular "hydroiminiumation" of alkenes: application to the synthesis of conjugate acids of cyclic alkyl amino carbenes (CAACs).

Authors:  Rodolphe Jazzar; Rian D Dewhurst; Jean-Baptiste Bourg; Bruno Donnadieu; Yves Canac; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Stereochemistry and mechanism of the Brønsted acid catalyzed intramolecular hydrofunctionalization of an unactivated cyclic alkene.

Authors:  Rachel E McKinney Brooner; Ross A Widenhoefer
Journal:  Chemistry       Date:  2011-04-19       Impact factor: 5.236

6.  Serendipitous discovery of the catalytic hydroammoniumation and methylamination of alkynes.

Authors:  Xiaoming Zeng; Rei Kinjo; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

  6 in total

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