Literature DB >> 11895420

Transmetalation of palladium enolate and its application in palladium-catalyzed homocoupling of alkynes: a room-temperature, highly efficient route to make diynes.

Aiwen Lei1, Manisha Srivastava, Xumu Zhang.   

Abstract

A novel pathway for the homocoupling reaction has been achieved using a similar protocol as the cross-coupling reaction. Ethyl bromoacetate is chosen to initiate the coupling reaction through oxidative addition to a Pd(0) species, and an PdBr(enolate) intermediate is formed. This intermediate can undergo double transmetalation with an alkynyl copper reagent, and reductive elimination produces a variety of diynes in high yields.

Entities:  

Year:  2002        PMID： 11895420     DOI： 10.1021/jo011098i

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


  8 in total

1.  Anionic four-electron donor-based palladacycles as catalysts for addition reactions of arylboronic acids with alpha,beta-unsaturated ketones, aldehydes, and alpha-ketoesters.

Authors:  Ping He; Yong Lu; Cheng-Guo Dong; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

2.  Design, synthesis, and subtype selectivity of 3,6-disubstituted β-carbolines at Bz/GABA(A)ergic receptors. SAR and studies directed toward agents for treatment of alcohol abuse.

Authors:  Wenyuan Yin; Samarpan Majumder; Terry Clayton; Steven Petrou; Michael L VanLinn; Ojas A Namjoshi; Chunrong Ma; Brett A Cromer; Bryan L Roth; Donna M Platt; James M Cook
Journal:  Bioorg Med Chem       Date:  2010-09-29       Impact factor: 3.641

3.  Pd-catalyzed alkynylation of 2-chloroacetates and 2-chloroacetamides with potassium alkynyltrifluoroborates.

Authors:  Gary A Molander; Kaitlin M Traister
Journal:  Org Lett       Date:  2013-09-16       Impact factor: 6.005

4.  A facile copper(I)-catalyzed homocoupling of terminal alkynes to 1,3-diynes with diaziridinone under mild conditions.

Authors:  Yingguang Zhu; Yian Shi
Journal:  Org Biomol Chem       Date:  2013-11-21       Impact factor: 3.876

5.  Homocoupling of aryl halides in flow: Space integration of lithiation and FeCl(3) promoted homocoupling.

Authors:  Aiichiro Nagaki; Yuki Uesugi; Yutaka Tomida; Jun-Ichi Yoshida
Journal:  Beilstein J Org Chem       Date:  2011-08-02       Impact factor: 2.883

6.  General Immobilization of Ultrafine Alloyed Nanoparticles within Metal-Organic Frameworks with High Loadings for Advanced Synergetic Catalysis.

Authors:  Fengfeng Chen; Kui Shen; Junying Chen; Xianfeng Yang; Jie Cui; Yingwei Li
Journal:  ACS Cent Sci       Date:  2019-01-07       Impact factor: 14.553

7.  Microwave assisted Suzuki-Miyaura and Ullmann type homocoupling reactions of 2- and 3-halopyridines using a Pd(OAc)2/benzimidazolium salt and base catalyst system.

Authors:  Ulkü Yılmaz; Selma Deniz; Hasan Küçükbay; Nihat Sireci
Journal:  Molecules       Date:  2013-03-25       Impact factor: 4.411

8.  A General and Highly Selective Palladium-Catalyzed Hydroamidation of 1,3-Diynes.

Authors:  Jiawang Liu; Carolin Schneider; Ji Yang; Zhihong Wei; Haijun Jiao; Robert Franke; Ralf Jackstell; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2020-10-27       Impact factor: 15.336
  8 in total

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