Literature DB >> 19673487

Gold-catalyzed cascade Friedel-Crafts/furan-alkyne cycloisomerizations for the highly efficient synthesis of arylated (Z)-enones or -enals.

Yifeng Chen1, Yuhua Lu, Guijie Li, Yuanhong Liu.   

Abstract

An efficient domino approach for the synthesis of arylated (Z)-enones or -enals through gold(I)-catalyzed reactions of enynols with furans was developed. PPh(3)AuNTf(2) was found to be an excellent catalyst to catalyze both of the Friedel-Crafts and furan/alkyne cyclization reactions in the same vessel. This method offers several advantages such as high stereoselectivities, mild reaction conditions, and easily accessible starting materials.

Entities:  

Year:  2009        PMID: 19673487     DOI: 10.1021/ol901408u

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


  6 in total

1.  Synthesis of novel isoquinolinone and 1,2-dihydroisoquinoline scaffolds via Ugi reaction and ring opening reaction of furans.

Authors:  Fei Ji; Wen-bin Yi; Mu Sun; Mei-fang Lv; Chun Cai
Journal:  Mol Divers       Date:  2013-03-20       Impact factor: 2.943

2.  Brönsted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans.

Authors:  Alexey Kuznetsov; Anton Makarov; Aleksandr E Rubtsov; Alexander V Butin; Vladimir Gevorgyan
Journal:  J Org Chem       Date:  2013-11-20       Impact factor: 4.354

3.  Stereocontrolled 1,3-phosphatyloxy and 1,3-halogen migration relay toward highly functionalized 1,3-dienes.

Authors:  Roohollah Kazem Shiroodi; Alexander S Dudnik; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2012-04-12       Impact factor: 15.419

4.  Au-Cavitands: Size governed arene-alkyne cycloisomerization.

Authors:  Lisa E Rusali; Michael P Schramm
Journal:  Tetrahedron Lett       Date:  2020-08-16       Impact factor: 2.415

5.  Recent advances in the gold-catalyzed additions to C-C multiple bonds.

Authors:  He Huang; Yu Zhou; Hong Liu
Journal:  Beilstein J Org Chem       Date:  2011-07-04       Impact factor: 2.883

6.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

  6 in total

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