Literature DB >> 19708697

Condensation reactions to form oxazoline-substituted potassium organotrifluoroborates.

Gary A Molander1, Wilma Febo-Ayala, Ludivine Jean-Gérard.   

Abstract

A library of oxazoline-substituted potassium organotrifluoroborates was prepared via the condensation of various potassium formyl-substituted aryl- and heteroaryltrifluoroborates with tosylmethyl isocyanide under basic conditions. The efficient Suzuki-Miyaura cross-coupling of products thus formed to various aryl bromides was achieved in good yields. The method allows the facile preparation of oxazole-containing triaromatic products in two steps from simple potassium formyl-substituted aryl- or heteroaryltrifluoroborates.

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Year:  2009        PMID： 19708697      PMCID： PMC2749650          DOI： 10.1021/ol901395c

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


  9 in total

1.  Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.

Authors:  Gary A Molander; Noel Ellis
Journal:  Acc Chem Res       Date:  2007-01-26       Impact factor: 22.384

Review 2.  Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors:  Sylvain Darses; Jean-Pierre Genet
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

3.  Suzuki coupling of oxazoles.

Authors:  Emmanuel Ferrer Flegeau; Matthew E Popkin; Michael F Greaney
Journal:  Org Lett       Date:  2006-06-08       Impact factor: 6.005

4.  Synthesis of functionalized organotrifluoroborates via the 1,3-dipolar cycloaddition of azides.

Authors:  Gary A Molander; Jungyeob Ham
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

5.  A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates.

Authors:  David M Knapp; Eric P Gillis; Martin D Burke
Journal:  J Am Chem Soc       Date:  2009-05-27       Impact factor: 15.419

6.  Regioselective palladium cross-coupling of 2,4-dihalooxazoles: convergent synthesis of trisoxazoles.

Authors:  Emmanuel Ferrer Flegeau; Matthew E Popkin; Michael F Greaney
Journal:  J Org Chem       Date:  2008-03-12       Impact factor: 4.354

7.  Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates.

Authors:  Gary A Molander; Belgin Canturk; Lauren E Kennedy
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

8.  Ethyl 2-chlorooxazole-4-carboxylate: a versatile intermediate for the synthesis of substituted oxazoles.

Authors:  Kevin J Hodgetts; Mark T Kershaw
Journal:  Org Lett       Date:  2002-08-22       Impact factor: 6.005

9.  Synthesis and absolute structure of manzacidin B.

Authors:  Tetsuro Shinada; Eijiro Ikebe; Kentaro Oe; Kosuke Namba; Masanori Kawasaki; Yasufumi Ohfune
Journal:  Org Lett       Date:  2007-04-06       Impact factor: 6.005
  9 in total
  2 in total

1.  Oxidative condensations to form benzimidazole-substituted potassium organotrifluoroborates.

Authors:  Gary A Molander; Kehinde Ajayi
Journal:  Org Lett       Date:  2012-08-08       Impact factor: 6.005

2.  Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling.

Authors:  Gary A Molander; Belgin Canturk
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
  2 in total

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