Literature DB >> 20565123

Copper-catalyzed alkynylation of amides with potassium alkynyltrifluoroborates: a room-temperature, base-free synthesis of ynamides.

Kévin Jouvin1, François Couty, Gwilherm Evano.   

Abstract

An efficient copper-mediated method for the coupling of potassium alkynyltrifluoroborates with nitrogen nucleophiles is reported. This reaction provides the first base-free and room-temperature synthesis of ynamides and allows for an easy preparation of these useful building blocks.

Entities:  

Year:  2010        PMID： 20565123     DOI： 10.1021/ol101322k

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


  9 in total

1.  Batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones. Application to the synthesis of polycyclic aromatic and heteroaromatic compounds.

Authors:  Thomas P Willumstad; Olesya Haze; Xiao Yin Mak; Tin Yiu Lam; Yu-Pu Wang; Rick L Danheiser
Journal:  J Org Chem       Date:  2013-10-28       Impact factor: 4.354

2.  N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

Authors:  Kyle A DeKorver; Whitney L Johnson; Yu Zhang; Richard P Hsung; Huifang Dai; Jun Deng; Andrew G Lohse; Yan-Shi Zhang
Journal:  J Org Chem       Date:  2011-05-24       Impact factor: 4.354

3.  Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases.

Authors:  Sebastian A Testero; Renee Bouley; Jed F Fisher; Mayland Chang; Shahriar Mobashery
Journal:  Bioorg Med Chem Lett       Date:  2010-12-29       Impact factor: 2.823

4.  S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Tetrahedron Lett       Date:  2015-05-06       Impact factor: 2.415

5.  Ynamide carbopalladation: a flexible route to mono-, bi- and tricyclic azacycles.

Authors:  Craig D Campbell; Rebecca L Greenaway; Oliver T Holton; P Ross Walker; Helen A Chapman; C Adam Russell; Greg Carr; Amber L Thomson; Edward A Anderson
Journal:  Chemistry       Date:  2015-07-16       Impact factor: 5.236

6.  Copper-catalyzed direct alkylation of heteroarenes.

Authors:  Cédric Theunissen; Jianjun Wang; Gwilherm Evano
Journal:  Chem Sci       Date:  2017-03-20       Impact factor: 9.825

7.  Microwave-enhanced cross-coupling reactions involving alkynyltrifluoroborates with aryl bromides.

Authors:  Vitali Coltuclu; Eric Dadush; Abhijit Naravane; George W Kabalka
Journal:  Molecules       Date:  2013-01-29       Impact factor: 4.411

8.  Intramolecular carbolithiation of N-allyl-ynamides: an efficient entry to 1,4-dihydropyridines and pyridines - application to a formal synthesis of sarizotan.

Authors:  Wafa Gati; Mohamed M Rammah; Mohamed B Rammah; Gwilherm Evano
Journal:  Beilstein J Org Chem       Date:  2012-12-21       Impact factor: 2.883

9.  Harnessing the Electrophilicity of Keteniminium Ions: A Simple and Straightforward Entry to Tetrahydropyridines and Piperidines from Ynamides.

Authors:  Morgan Lecomte; Gwilherm Evano
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-02       Impact factor: 15.336
  9 in total

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