Literature DB >> 22591008

General and selective head-to-head dimerization of terminal alkynes proceeding via hydropalladation pathway.

Claire Jahier1, Olga V Zatolochnaya, Nickolay V Zvyagintsev, Valentine P Ananikov, Vladimir Gevorgyan.   

Abstract

A general highly regio- and stereoselective palladium-catalyzed head-to-head dimerization reaction of terminal acetylenes is presented. This methodology allows for the efficient synthesis of a variety of 1,4-enynes as single E stereoisomers. Computational studies reveal that this dimerization reaction proceeds via the hydropalladation pathway.

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Year:  2012        PMID: 22591008     DOI: 10.1021/ol3010936

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


  6 in total

Review 1.  Transition metal-catalyzed couplings of alkynes to 1,3-enynes: modern methods and synthetic applications.

Authors:  Barry M Trost; James T Masters
Journal:  Chem Soc Rev       Date:  2016-02-01       Impact factor: 54.564

2.  Rhodium-catalyzed chemo- and regioselective cross-dimerization of two terminal alkynes.

Authors:  Hua-Dong Xu; Ren-Wei Zhang; Xiaoxun Li; Suyu Huang; Weiping Tang; Wen-Hao Hu
Journal:  Org Lett       Date:  2013-01-28       Impact factor: 6.005

3.  Revealing the unusual role of bases in activation/deactivation of catalytic systems: O-NHC coupling in M/NHC catalysis.

Authors:  Victor M Chernyshev; Oleg V Khazipov; Maxim A Shevchenko; Andrey Yu Chernenko; Alexander V Astakhov; Dmitry B Eremin; Dmitry V Pasyukov; Alexey S Kashin; Valentine P Ananikov
Journal:  Chem Sci       Date:  2018-06-06       Impact factor: 9.825

4.  Hydroalkynylative cyclization of 1,6-enynes with terminal alkynes.

Authors:  Qi Teng; Nuligonda Thirupathi; Chen-Ho Tung; Zhenghu Xu
Journal:  Chem Sci       Date:  2019-06-13       Impact factor: 9.825

5.  Atom-Economical Cross-Coupling of Internal and Terminal Alkynes to Access 1,3-Enynes.

Authors:  Mingyu Liu; Tianhua Tang; Omar Apolinar; Rei Matsuura; Carl A Busacca; Bo Qu; Daniel R Fandrick; Olga V Zatolochnaya; Chris H Senanayake; Jinhua J Song; Keary M Engle
Journal:  J Am Chem Soc       Date:  2021-03-08       Impact factor: 15.419

6.  Terminal Alkyne Coupling Reactions through a Ring: Mechanistic Insights and Regiochemical Switching.

Authors:  Caroline M Storey; Matthew R Gyton; Rhiann E Andrew; Adrian B Chaplin
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-20       Impact factor: 15.336

  6 in total

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