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Literature DB >> 24971828

General silver-catalyzed hydroazidation of terminal alkynes by combining TMS-N3 and H2O: synthesis of vinyl azides.

Abstract

A general hydroazidation of unactivated alkynes using silver catalysis is reported. The reactions of diverse terminal alkynes with trimethylsilyl azide (TMS-N(3)) in the presence of H(2)O afforded the corresponding vinyl azides in good to excellent yields. This reaction has a broad substrate scope, good functional group tolerance, simple operation, and high reaction efficiency, thus providing an easy access to various functionalized vinyl azides.

Entities: Chemical Disease

Year: 2014 PMID： 24971828 DOI： 10.1021/ol501661k

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

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Cited

7 in total

1. Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an N-Unsubstituted 1,2,3-Triazol-4-yl Moiety.

Authors: Zhiwei Wen; Paloma R Tuttle; A Hasan Howlader; Anna Vasilyeva; Laura Gonzalez; Antonija Tangar; Ruipeng Lei; Eduardo E Laverde; Yuan Liu; Jaroslava Miksovska; Stanislaw F Wnuk
Journal: J Org Chem Date: 2019-03-06 Impact factor: 4.354

2. Electron-Mediated Aminyl and Iminyl Radicals from C5 Azido-Modified Pyrimidine Nucleosides Augment Radiation Damage to Cancer Cells.

Authors: Zhiwei Wen; Jufang Peng; Paloma R Tuttle; Yaou Ren; Carol Garcia; Dipra Debnath; Sunny Rishi; Cameron Hanson; Samuel Ward; Anil Kumar; Yanfeng Liu; Weixi Zhao; Peter M Glazer; Yuan Liu; Michael D Sevilla; Amitava Adhikary; Stanislaw F Wnuk
Journal: Org Lett Date: 2018-11-20 Impact factor: 6.005

General silver-catalyzed hydroazidation of terminal alkynes by combining TMS-N3 and H2O: synthesis of vinyl azides.

1. Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an N-Unsubstituted 1,2,3-Triazol-4-yl Moiety.

2. Electron-Mediated Aminyl and Iminyl Radicals from C5 Azido-Modified Pyrimidine Nucleosides Augment Radiation Damage to Cancer Cells.

3. Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes.

Review 4. Metal-Catalysed Azidation of Organic Molecules.

5. Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative N-incorporation.

6. Iron-catalyzed carboazidation of alkenes and alkynes.

7. Divergent synthesis of chiral cyclic azides via asymmetric cycloaddition reactions of vinyl azides.