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Literature DB >> 19453151

Iron-catalyzed amidation of alkynyl bromides: a facile route for the preparation of ynamides.

Bangben Yao¹, Zunjun Liang, Tianmin Niu, Yuhong Zhang.

Abstract

A facile route to obtain ynamides in high yields was described. The products were achieved through the iron-catalyzed C-N coupling reaction of amides with alkynyl bromides in the presence of 20 mol % of N,N'-dimethylethane-1,2-diamine (DMEDA).

Entities: Chemical

Year: 2009 PMID： 19453151 DOI： 10.1021/jo900595c

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

10 in total

Review 1. Ynamides: a modern functional group for the new millennium.

Authors: Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal: Chem Rev Date: 2010-09-08 Impact factor: 60.622

2. A divergent mechanistic course of Pd(0)-catalyzed aza-Claisen rearrangement and aza-Rautenstrauch-type cyclization of N-allyl ynamides.

Authors: Kyle A Dekorver; Richard P Hsung; Andrew G Lohse; Yu Zhang
Journal: Org Lett Date: 2010-04-16 Impact factor: 6.005

3. 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

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. A Stereoselective Intramolecular Cyclopropanation via a De Novo Class of Push-Pull Carbenes Derived from DMDO-Epoxidations of Chiral Ynamides.

Authors: Hongyan Li; Jennifer E Antoline; Jin-Haek Yang; Ziyad F Al-Rashid; Richard P Hsung
Journal: New J Chem Date: 2010-01-01 Impact factor: 3.591

Iron-catalyzed amidation of alkynyl bromides: a facile route for the preparation of ynamides.

Review 1. Ynamides: a modern functional group for the new millennium.

2. A divergent mechanistic course of Pd(0)-catalyzed aza-Claisen rearrangement and aza-Rautenstrauch-type cyclization of N-allyl ynamides.

3. 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.

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

5. A Stereoselective Intramolecular Cyclopropanation via a De Novo Class of Push-Pull Carbenes Derived from DMDO-Epoxidations of Chiral Ynamides.

6. Facile synthesis of α-alkoxyl amides via scandium-catalyzed oxidative reaction between ynamides and alcohols.

7. Highly substituted 2-amido-furans from Rh(II)-catalyzed cyclopropenations of ynamides.

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

9. Direct oxidation of N-ynylsulfonamides into N-sulfonyloxoacetamides with DMSO as a nucleophilic oxidant.

Review 10. Preparation and Utility of N-Alkynyl Azoles in Synthesis.