Literature DB >> 26279591

Branched/linear selectivity in palladium-catalyzed allyl-allyl cross-couplings: The role of ligands.

Michael J Ardolino1, James P Morken1.   

Abstract

While Pd-catalyzed allyl-allyl cross-couplings in the presence of small-bite-angle bidentate ligands reliably furnish the branched regioisomer with high levels of selectivity, cross-couplings in the presence of large-bite-angle bidentate ligands give varying, often unpredictable, levels of selectivity. In a combined computational and experimental study, we probe the underlying features that govern the regioselectivity in these metal-catalyzed cross-couplings.

Entities:  

Keywords:  Allylation; Bite Angle; Cross-coupling; Pd catalysis

Year:  2015        PMID： 26279591      PMCID： PMC4531376          DOI： 10.1016/j.tet.2015.05.015

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  19 in total

1.  A stereospecific ruthenium-catalyzed allylic alkylation.

Authors:  Barry M Trost; Pierre L Fraisse; Zachary T Ball
Journal:  Angew Chem Int Ed Engl       Date:  2002-03-15       Impact factor: 15.336

2.  Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings.

Authors:  Michael J Ardolino; James P Morken
Journal:  J Am Chem Soc       Date:  2012-05-17       Impact factor: 15.419

3.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

Authors: 
Journal:  Phys Rev B Condens Matter       Date:  1988-01-15

4.  Iridium-catalyzed enantioselective allyl-allylsilane cross-coupling.

Authors:  James Y Hamilton; Nicole Hauser; David Sarlah; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-11       Impact factor: 15.336

5.  Diastereocontrol in asymmetric allyl-allyl cross-coupling: stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides.

Authors:  Laura A Brozek; Michael J Ardolino; James P Morken
Journal:  J Am Chem Soc       Date:  2011-10-05       Impact factor: 15.419

6.  Iridium-catalyzed enantioselective allyl-alkene coupling.

Authors:  James Y Hamilton; David Sarlah; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2014-02-12       Impact factor: 15.419

7.  Intramolecular coupling of allyl carboxylates with allyl stannanes and allyl silanes: a new type of reductive elimination reaction?

Authors:  María Méndez; Juan M Cuerva; Enrique Gómez-Bengoa; Diego J Cárdenas; Antonio M Echavarren
Journal:  Chemistry       Date:  2002-08-16       Impact factor: 5.236

8.  Palladium(0) versus nickel(0) catalysis in selective functional-group-tolerant sp(3)-sp(3) carbon-carbon bond formations.

Authors:  Emmanuel Ferrer Flegeau; Uwe Schneider; Shū Kobayashi
Journal:  Chemistry       Date:  2009-11-16       Impact factor: 5.236

9.  Copper-catalyzed enantioselective allyl-allyl cross-coupling.

Authors:  Valentín Hornillos; Manuel Pérez; Martín Fañanás-Mastral; Ben L Feringa
Journal:  J Am Chem Soc       Date:  2013-02-01       Impact factor: 15.419

10.  Congested C-C bonds by Pd-catalyzed enantioselective allyl-allyl cross-coupling, a mechanism-guided solution.

Authors:  Michael J Ardolino; James P Morken
Journal:  J Am Chem Soc       Date:  2014-04-29       Impact factor: 15.419
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