Literature DB >> 15113193

Phosphine catalyzed alpha-arylation of enones and enals using hypervalent bismuth reagents: regiospecific enolate arylation via nucleophilic catalysis.

Phillip K Koech1, Michael J Krische.   

Abstract

Exposure of enones and enals to 20 mol % tributylphosphine in the presence of triarylbismuth(V) dichlorides results in regiospecific aryl transfer to the alpha-position of the enone or enal pronucleophile. These results represent the first examples of enolate arylation under the conditions of nucleophilic catalysis.

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Year:  2004        PMID： 15113193     DOI： 10.1021/ja048987i

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 in total

1.  Recent advances in heterolytic nucleofugal leaving groups.

Authors:  Salvatore D Lepore; Deboprosad Mondal
Journal:  Tetrahedron       Date:  2007-06-11       Impact factor: 2.457

Review 2.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

3.  Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents.

Authors:  Felipe Cesar Sousa E Silva; Nguyen T Van; Sarah E Wengryniuk
Journal:  J Am Chem Soc       Date:  2019-12-27       Impact factor: 15.419

4.  Palladium-catalyzed regiocontrolled alpha-arylation of trimethylsilyl enol ethers with aryl halides.

Authors:  Tetsuo Iwama; Viresh H Rawal
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

5.  Asymmetric total synthesis of the iridoid beta-glucoside (+)-geniposide via phosphine organocatalysis.

Authors:  Regan A Jones; Michael J Krische
Journal:  Org Lett       Date:  2009-04-16       Impact factor: 6.005

6.  Copper-assisted palladium(II)-catalyzed direct arylation of cyclic enaminones with arylboronic acids.

Authors:  Yong Wook Kim; Micah J Niphakis; Gunda I Georg
Journal:  J Org Chem       Date:  2012-10-22       Impact factor: 4.354

7.  Efficient synthesis of 3H-indoles enabled by the lead-mediated α-arylation of β-ketoesters or γ-lactams using aryl azides.

Authors:  Fei Zhou; Tom G Driver
Journal:  Org Lett       Date:  2014-05-27       Impact factor: 6.005

8.  α-Arylation of Carbonyl Compounds through Oxidative C-C Bond Activation.

Authors:  Jing Li; Adriano Bauer; Giovanni Di Mauro; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-06       Impact factor: 16.823

9.  Formal Enone α-Arylation via I(III)-Mediated Aryl Migration/Elimination.

Authors:  Bruna S Martins; Daniel Kaiser; Adriano Bauer; Irmgard Tiefenbrunner; Nuno Maulide
Journal:  Org Lett       Date:  2021-02-26       Impact factor: 6.005

Review 10.  Bismuth Redox Catalysis: An Emerging Main-Group Platform for Organic Synthesis.

Authors:  Hye Won Moon; Josep Cornella
Journal:  ACS Catal       Date:  2022-01-07       Impact factor: 13.084
  10 in total

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