Literature DB >> 24040828

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

Gary A Molander1, Kaitlin M Traister.   

Abstract

The synthesis of β,γ-alkynyl esters and amides using air-stable potassium alkynyltrifluoroborates as nucleophilic partners in a mild Suzuki-Miyaura cross-coupling reaction has been achieved. Propargyl esters and amides were obtained in high yields using a low catalyst loading, and the substrate scope of the reaction has been significantly improved over previous methods.

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Year:  2013        PMID: 24040828      PMCID: PMC3820111          DOI: 10.1021/ol402391z

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


  7 in total

1.  A straightforward and mild synthesis of functionalized 3-alkynoates.

Authors:  Andrés Suárez; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-05       Impact factor: 15.336

2.  Mechanistic origin of antagonist effects of usual anionic bases (OH-, CO3(2-)) as modulated by their countercations (Na+, Cs+, K+) in palladium-catalyzed Suzuki-Miyaura reactions.

Authors:  Christian Amatore; Anny Jutand; Gaëtan Le Duc
Journal:  Chemistry       Date:  2012-04-18       Impact factor: 5.236

3.  Organotrifluoroborate hydrolysis: boronic acid release mechanism and an acid-base paradox in cross-coupling.

Authors:  Alastair J J Lennox; Guy C Lloyd-Jones
Journal:  J Am Chem Soc       Date:  2012-04-19       Impact factor: 15.419

4.  Palladium-catalyzed alkynylation of secondary α-bromo carbonyl compounds via Stille coupling.

Authors:  Jun Yong Kang; Brian T Connell
Journal:  J Org Chem       Date:  2011-07-19       Impact factor: 4.354

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

Authors:  Aiwen Lei; Manisha Srivastava; Xumu Zhang
Journal:  J Org Chem       Date:  2002-03-22       Impact factor: 4.354

6.  Pd-catalyzed cross-coupling of potassium alkenyltrifluoroborates with 2-chloroacetates and 2-chloroacetamides.

Authors:  Gary A Molander; Thiago Barcellos; Kaitlin M Traister
Journal:  Org Lett       Date:  2013-06-14       Impact factor: 6.005

7.  Palladium-catalyzed α-arylation of 2-chloroacetates and 2-chloroacetamides.

Authors:  Gary A Molander; Kaitlin M Traister; Thiago Barcellos
Journal:  J Org Chem       Date:  2013-04-09       Impact factor: 4.354

  7 in total
  1 in total

Review 1.  The Fascinating Chemistry of α-Haloamides.

Authors:  Anna Fantinati; Vinicio Zanirato; Paolo Marchetti; Claudio Trapella
Journal:  ChemistryOpen       Date:  2020-01-13       Impact factor: 2.911

  1 in total

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