Literature DB >> 28203678

Brønsted acid-catalyzed α-halogenation of ynamides from halogenated solvents and pyridine-N-oxides.

Seung Woo Kim1, Tae-Woong Um1, Seunghoon Shin1.   

Abstract

The keteniminium ions generated from the protonation of ynamides formed reversible adducts with counter anions and pyridine-N-oxides as well as halogenated solvents. Above 80 °C, the halonium ions selectively undergo a rate-limiting attack by pyridine-N-oxides, leading to (E)-haloenamides in good yields.

Entities:  

Year:  2017        PMID： 28203678     DOI： 10.1039/c6cc10286g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  3 in total

1.  Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate.

Authors:  Rosario Merino-García; Samuel Hernández-Anzaldo; Yasmi Reyes-Ortega
Journal:  J Vis Exp       Date:  2018-04-24       Impact factor: 1.355

2.  Metal-free, Regio-, and Stereo-Controlled Hydrochlorination and Hydrobromination of Ynones and Ynamides.

Authors:  Xiaojun Zeng; Zhichao Lu; Shiwen Liu; Gerald B Hammond; Bo Xu
Journal:  J Org Chem       Date:  2017-12-07       Impact factor: 4.354

3.  Synthesis of γ-substituted carbonyl compounds from DMSO-mediated oxidation of enynamides: mechanistic insights and carbon- and hetero-functionalizations.

Authors:  Quynh H Nguyen; Nguyen H Nguyen; Hanbyul Kim; Seunghoon Shin
Journal:  Chem Sci       Date:  2019-08-12       Impact factor: 9.825
  3 in total

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