Literature DB >> 16557307

Regioselectivity in the Sonogashira coupling of 4,6-dichloro-2-pyrone.

Ian J S Fairlamb1, Ciara T O'Brien, Zhenyang Lin, King Chung Lam.   

Abstract

The Sonogashira cross-coupling of 4,6-dichloro-2-pyrone with terminal acetylenes proceeds in good yields and high regioselectivity for the 6-position; dibenzylidene acetone (dba) type ligands play a non-innocent role in reactions mediated by Pd(dba)2/PPh3; theoretical studies indicate that C-6 oxidative addition is favoured both kinetically and thermodynamically.

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Year:  2006        PMID： 16557307     DOI： 10.1039/b518232h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  4 in total

1.  Computational study of the Sonogashira cross-coupling reaction in the gas phase and in dichloromethane solution.

Authors:  Lauri Sikk; Jaana Tammiku-Taul; Peeter Burk; András Kotschy
Journal:  J Mol Model       Date:  2011-12-10       Impact factor: 1.810

2.  Theoretical bond dissociation energies of halo-heterocycles: trends and relationships to regioselectivity in palladium-catalyzed cross-coupling reactions.

Authors:  Yeimy Garcia; Franziska Schoenebeck; Claude Y Legault; Craig A Merlic; K N Houk
Journal:  J Am Chem Soc       Date:  2009-05-13       Impact factor: 15.419

3.  Palladium-catalyzed highly regioselective mono and double Sonogashira cross-coupling reactions of 5-substituted-1,2,3-triiodobenzene under ambient conditions.

Authors:  Raed M Al-Zoubi; Mothana K Al-Omari; Walid K Al-Jammal; Michael J Ferguson
Journal:  RSC Adv       Date:  2020-04-24       Impact factor: 3.361

4.  Site-selective Suzuki-Miyaura coupling of heteroaryl halides - understanding the trends for pharmaceutically important classes.

Authors:  Joshua Almond-Thynne; David C Blakemore; David C Pryde; Alan C Spivey
Journal:  Chem Sci       Date:  2016-08-09       Impact factor: 9.825
  4 in total

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