Literature DB >> 15327305

Intramolecular C-N bond addition of amides to alkynes using platinum catalyst.

Tomohiro Shimada1, Itaru Nakamura, Yoshinori Yamamoto.   

Abstract

The intramolecular aminoacylation of alkynes using ortho-alkynylacetanilides proceeds in very high yields in the presence of PtCl2 catalyst. This reaction provides not only a useful procedure for synthesizing 2,3-disubstituted indoles at once from ortho-alkynylaniline derivatives, but also an interesting mechanistic aspect; the intramolecular C-N bond addition of amides to alkynes takes place readily in the presence of Pt(II) catalyst.

Entities:  

Year:  2004        PMID: 15327305     DOI: 10.1021/ja047542r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  13 in total

1.  Copper-, Silver-, and Gold-Catalyzed Migratory Cycloisomerizations Leading to Heterocyclic Five-Membered Rings.

Authors:  Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Aldrichimica Acta       Date:  2010       Impact factor: 3.667

2.  Structural characterization of N-protonated amides: regioselective N-activation of medium-bridged twisted lactams.

Authors:  Michal Szostak; Lei Yao; Victor W Day; Douglas R Powell; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

3.  The Neber route to substituted indoles.

Authors:  Douglass F Taber; Weiwei Tian
Journal:  J Am Chem Soc       Date:  2006-02-01       Impact factor: 15.419

4.  A Brief Survey of our Contribution to Stable Carbene Chemistry.

Authors:  David Martin; Mohand Melaimi; Michele Soleilhavoup; Guy Bertrand
Journal:  Organometallics       Date:  2011-09-22       Impact factor: 3.876

Review 5.  Stable cyclic carbenes and related species beyond diaminocarbenes.

Authors:  Mohand Melaimi; Michèle Soleilhavoup; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

6.  A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  Synlett       Date:  2010-03-01       Impact factor: 2.454

7.  Nickel-Catalyzed Dearomative trans-1,2-Carboamination.

Authors:  Lucas W Hernandez; Ulrich Klöckner; Jola Pospech; Lilian Hauss; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-03-23       Impact factor: 15.419

8.  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

9.  Triflic acid controlled successive annelation of aromatic sulfonamides: An efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles.

Authors:  Mohammed Abid; Liliana Teixeira; Béla Török
Journal:  Tetrahedron Lett       Date:  2007-06-04       Impact factor: 2.415

10.  One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines.

Authors:  Jonathan P Brand; Clara Chevalley; Jérôme Waser
Journal:  Beilstein J Org Chem       Date:  2011-05-04       Impact factor: 2.883

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