Literature DB >> 15771503

Direct palladium-catalyzed arylation of cyclopropenes.

Stepan Chuprakov1, Michael Rubin, Vladimir Gevorgyan.   

Abstract

The first examples of direct palladium-catalyzed arylation and heteroarylation of cyclopropenes have been demonstrated. This method allows for efficient synthesis of various tetrasubstituted cyclopropenes, incuding nonracemic cyclopropenes, which are not available via known asymmetric cyclopropenation methods. Mechanistic studies strongly suggest an electrophilic path for this Heck-type transformation.

Entities:  

Year:  2005        PMID： 15771503     DOI： 10.1021/ja042380k

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


  6 in total

1.  Regiodivergent metal-catalyzed rearrangement of 3-iminocyclopropenes into N-fused heterocycles.

Authors:  Stepan Chuprakov; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2007-09-25       Impact factor: 6.005

2.  Studies on the stability of cycloprop-2-ene carboxylate dianions and reactions with electrophiles.

Authors:  Laural A Fisher; Joseph M Fox
Journal:  J Org Chem       Date:  2008-10-14       Impact factor: 4.354

3.  Functionalized Cyclopropenes and Methylenecyclopropenes from Dianions of 3-Hydroxymethylcyclopropenes.

Authors:  Matthew D Hassink; Joseph M Fox
Journal:  Synthesis (Stuttg)       Date:  2012       Impact factor: 3.157

4.  Regioselective synthesis of multisubstituted furans via metalloradical cyclization of alkynes with α-diazocarbonyls: construction of functionalized α-oligofurans.

Authors:  Xin Cui; Xue Xu; Lukasz Wojtas; Martin M Kim; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2012-12-03       Impact factor: 15.419

5.  Catalytic Synthesis of Trifluoromethyl Cyclopropenes and Oligo-Cyclopropenes.

Authors:  Uyen P N Tran; Renè Hommelsheim; Zhen Yang; Claire Empel; Katharina J Hock; Thanh V Nguyen; René M Koenigs
Journal:  Chemistry       Date:  2020-01-20       Impact factor: 5.236

6.  Catalytic Synthesis of Cyclopropenium Cations with Rh-Carbynoids.

Authors:  Hang-Fei Tu; Aliénor Jeandin; Marcos G Suero
Journal:  J Am Chem Soc       Date:  2022-09-08       Impact factor: 16.383
  6 in total

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