Literature DB >> 22171540

Copper-catalyzed oxidative alkynylation of diaryl imines with terminal alkynes: a facile synthesis of ynimines.

Anouar Laouiti1, Mohamed M Rammah, Mohamed B Rammah, Jérome Marrot, François Couty, Gwilherm Evano.   

Abstract

An efficient copper-mediated method for the oxidative alkynylation of diaryl imines with terminal alkynes is reported. This reaction provides the first catalytic and general synthesis of ynimines and allows for an easy preparation of these useful building blocks. An improved copper-catalyzed oxidative dimerization of imines to azines and the synthesis of dienes and azadienes from ynimines are also described.
© 2011 American Chemical Society

Entities:  

Year:  2011        PMID： 22171540     DOI： 10.1021/ol2032152

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


  11 in total

1.  Electrochemical Strategy for Hydrazine Synthesis: Development and Overpotential Analysis of Methods for Oxidative N-N Coupling of an Ammonia Surrogate.

Authors:  Fei Wang; James B Gerken; Desiree M Bates; Yeon Jung Kim; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2020-06-29       Impact factor: 15.419

2.  SYNTHESIS OF DE NOVO CHIRAL γ-AMINO-YNAMIDES USING LITHIATED YNAMIDES. OBSERVATION OF A UNIQUE 5-ENDO-DIG CYCLIZATION WITH AN INVERSION OF S-CENTER.

Authors:  Xiao-Na Wang; Richard P Hsung; Sierra K Fox; Ming-Can Lv; Rui Qi
Journal:  Heterocycles       Date:  2014-01-01       Impact factor: 0.831

3.  Carbocyclization cascades of allyl ketenimines via aza-Claisen rearrangements of N-phosphoryl-N-allyl-ynamides.

Authors:  Kyle A DeKorver; Xiao-Na Wang; Mary C Walton; Richard P Hsung
Journal:  Org Lett       Date:  2012-03-13       Impact factor: 6.005

4.  Novel ynamide structural analogues and their synthetic transformations.

Authors:  Ting Lu; Richard P Hsung
Journal:  ARKIVOC       Date:  2014       Impact factor: 1.140

5.  Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence.

Authors:  Xiao-Na Wang; Gabrielle N Winston-McPherson; Mary C Walton; Yu Zhang; Richard P Hsung; Kyle A DeKorver
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

6.  A highly stereoselective addition of lithiated ynamides to Ellman-Davis chiral N-tert-butanesulfinyl imines.

Authors:  Xiao-Na Wang; Richard P Hsung; Rui Qi; Sierra K Fox; Ming-Can Lv
Journal:  Org Lett       Date:  2013-05-06       Impact factor: 6.005

7.  A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines. Observation of an Aza-Meyer-Schuster Rearrangement.

Authors:  Rui Qi; Xiao-Na Wang; Kyle A Dekorver; Yu Tang; Chao-Chao Wang; Qian Li; Hui Li; Ming-Can Lv; Qing Yu; Richard P Hsung
Journal:  Synthesis (Stuttg)       Date:  2013-07-01       Impact factor: 3.157

8.  Mechanistic insights into copper-catalyzed aerobic oxidative coupling of N-N bonds.

Authors:  Michael C Ryan; Yeon Jung Kim; James B Gerken; Fei Wang; Michael M Aristov; Joseph R Martinelli; Shannon S Stahl
Journal:  Chem Sci       Date:  2019-12-10       Impact factor: 9.825

9.  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

10.  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
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