Literature DB >> 15760233

A practical method for the synthesis of 2-alkynylpropenals.

Charnsak Thongsornkleeb1, Rick L Danheiser.   

Abstract

A general method for the preparation of 2-alkynyl acroleins is described beginning with vinyl iodide 5 and involving a combination of Sonogashira coupling and Dess-Martin oxidation. Critical to the success of this approach is the use of a special workup procedure for the oxidation step. The resultant enynals participate in a variety of addition reactions including aldol condensations and reactions with organolithium compounds.

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Year:  2005        PMID: 15760233      PMCID: PMC2897060          DOI: 10.1021/jo047869a

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


  1 in total

Review 1.  Palladium-catalyzed alkynylation.

Authors:  Ei-ichi Negishi; Luigi Anastasia
Journal:  Chem Rev       Date:  2003-05       Impact factor: 60.622

  1 in total
  5 in total

Review 1.  Chemistry of polyvalent iodine.

Authors:  Viktor V Zhdankin; Peter J Stang
Journal:  Chem Rev       Date:  2008-12       Impact factor: 60.622

2.  Rhodium-catalyzed chemo- and regioselective cross-dimerization of two terminal alkynes.

Authors:  Hua-Dong Xu; Ren-Wei Zhang; Xiaoxun Li; Suyu Huang; Weiping Tang; Wen-Hao Hu
Journal:  Org Lett       Date:  2013-01-28       Impact factor: 6.005

3.  Umpolung carbonyls enable direct allylation and olefination of carbohydrates.

Authors:  Jian Kan; Zhangpei Chen; Zihang Qiu; Leiyang Lv; Chenchen Li; Chao-Jun Li
Journal:  Sci Adv       Date:  2022-03-09       Impact factor: 14.136

4.  3D designed and printed chemical generators for on demand reagent synthesis.

Authors:  Sergey S Zalesskiy; Philip J Kitson; Przemyslaw Frei; Andrius Bubliauskas; Leroy Cronin
Journal:  Nat Commun       Date:  2019-12-02       Impact factor: 14.919

5.  Chemical Space Exploration of Oxetanes.

Authors:  Fernando Rodrigues de Sá Alves; Rafael M Couñago; Stefan Laufer
Journal:  Int J Mol Sci       Date:  2020-11-02       Impact factor: 5.923

  5 in total

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