Literature DB >> 16050689

Pd(CH3CN)2Cl2-catalyzed oxidative heterodimerization reaction of 2,3-allenamides and 1,2-allenyl ketones: an efficient synthesis of 4-(furan-3'-yl)-2(5H)-furanimines.

Shengming Ma1, Zhenhua Gu, Zhanqian Yu.   

Abstract

The Pd(II)-catalyzed oxidative heterodimerization reaction of 2,3-allenamides and 1,2-allenyl ketones was studied. It provides an efficient route for the synthesis of the polysubstituted 4-(furan-3'-yl)-2(5H)-furanimines, which are not readily available from the known methods. Due to the application of benzoquinone, the loadings of both the palladium catalyst and ketone have been greatly reduced for the oxidative heterodimerization of 2,3-allenamides and 1,2-allenyl ketones in acetic acid.

Entities:  

Year:  2005        PMID: 16050689     DOI: 10.1021/jo0507441

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


  5 in total

Review 1.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

2.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

3.  Regio- and stereoselective synthesis of cyclic imidates via electrophilic cyclization of 2-(1-alkynyl)benzamides. A correction.

Authors:  Saurabh Mehta; Tuanli Yao; Richard C Larock
Journal:  J Org Chem       Date:  2012-11-15       Impact factor: 4.354

4.  Solution-phase parallel synthesis of a multisubstituted cyclic imidate library.

Authors:  Saurabh Mehta; Jesse P Waldo; Benjamin Neuenswander; Gerald H Lushington; Richard C Larock
Journal:  ACS Comb Sci       Date:  2013-04-04       Impact factor: 3.784

5.  CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligands.

Authors:  Shuxu Gao; Yu Liu; Shengming Ma
Journal:  Beilstein J Org Chem       Date:  2011-04-07       Impact factor: 2.883

  5 in total

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