Literature DB >> 24766635

Copper-catalyzed regio- and stereoselective intermolecular three-component oxyarylation of allenes.

Taisuke Itoh1, Yohei Shimizu, Motomu Kanai.   

Abstract

A copper(II)-catalyzed intermolecular three-component oxyarylation of allenes using arylboronic acids as a carbon source and TEMPO as an oxygen source is described. The reaction proceeded under mild conditions with high regio- and stereoselectivity and functional group tolerance. A plausible reaction mechanism is proposed, involving carbocupration of allenes, homolysis of the intervening allylcopper(II), and a radical TEMPO trap.

Entities:  

Mesh：

Substances：

Year:  2014        PMID： 24766635     DOI： 10.1021/ol501022d

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


  6 in total

1.  Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters.

Authors:  Barbara J Casavant; Zainab M Khoder; Ilyas A Berhane; Sherry R Chemler
Journal:  Org Lett       Date:  2015-12-01       Impact factor: 6.005

2.  Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes.

Authors:  Kay Yeung; Rebecca E Ruscoe; James Rae; Alexander P Pulis; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-19       Impact factor: 15.336

Review 3.  Enantioselective copper catalysed, direct functionalisation of allenes via allyl copper intermediates.

Authors:  Alexander P Pulis; Kay Yeung; David J Procter
Journal:  Chem Sci       Date:  2017-06-08       Impact factor: 9.825

4.  Copper-Catalyzed Borylative Cross-Coupling of Allenes and Imines: Selective Three-Component Assembly of Branched Homoallyl Amines.

Authors:  James Rae; Kay Yeung; Joseph J W McDouall; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-03       Impact factor: 15.336

5.  Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes.

Authors:  H Surya Prakash Rao; A Veera Bhadra Rao
Journal:  Beilstein J Org Chem       Date:  2016-03-11       Impact factor: 2.883

6.  Cu-catalyzed C-C bond formation of vinylidene cyclopropanes with carbon nucleophiles.

Authors:  Jichao Chen; Shang Gao; Ming Chen
Journal:  Chem Sci       Date:  2019-10-09       Impact factor: 9.825
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.