Literature DB >> 17279765

Preparation and wittig reactions of organotrifluoroborato phosphonium ylides.

Gary A Molander1, Jungyeob Ham, Belgin Canturk.   

Abstract

[reaction: see text] Potassium [(trifluoroboratophenyl)methyl]triphenylphosphonium chlorides have been prepared from the corresponding benzyl chlorides and PPh3. In the presence of 1.2 equiv of K2CO3 and various aldehydes, these mixed salts are easily converted to the corresponding unsaturated organotrifluoroborates via the intermediate phosphorus ylides. A protocol for a one-pot transformation has also been developed.

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Year:  2007        PMID: 17279765      PMCID: PMC2556880          DOI: 10.1021/ol063043e

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


  16 in total

1.  Synthesis of unsaturated organotrifluoroborates via Wittig and Horner-Wadsworth-Emmons olefination.

Authors:  Gary A Molander; Ruth Figueroa
Journal:  J Org Chem       Date:  2006-08-04       Impact factor: 4.354

2.  Palladium-catalyzed cross-coupling reactions in total synthesis.

Authors:  K C Nicolaou; Paul G Bulger; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-18       Impact factor: 15.336

3.  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

4.  Room-temperature alkyl-alkyl Suzuki cross-coupling of alkyl bromides that possess beta hydrogens.

Authors:  M R Netherton; C Dai; K Neuschütz; G C Fu
Journal:  J Am Chem Soc       Date:  2001-10-17       Impact factor: 15.419

Review 5.  Carbon-carbon bonding made easy.

Authors:  Akira Suzuki
Journal:  Chem Commun (Camb)       Date:  2005-09-07       Impact factor: 6.222

6.  Synthesis of functionalized organotrifluoroborates via halomethyltrifluoroborates.

Authors:  Gary A Molander; Jungyeob Ham
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

7.  Amphidinolide B: asymmetric synthesis of a C7-C20 synthon.

Authors:  Apsara Gopalarathnam; Scott G Nelson
Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

8.  Oxidation of hydroxyl-substituted organotrifluoroborates.

Authors:  Gary A Molander; Daniel E Petrillo
Journal:  J Am Chem Soc       Date:  2006-08-02       Impact factor: 15.419

9.  Synthesis and evaluation of new omega-borono-alpha-amino acids as rat liver arginase inhibitors.

Authors:  Olivier Busnel; François Carreaux; Bertrand Carboni; Stephanie Pethe; Sandrine Vadon-Le Goff; Daniel Mansuy; Jean-Luc Boucher
Journal:  Bioorg Med Chem       Date:  2005-04-01       Impact factor: 3.641

10.  Rhodium-catalyzed tandem cyclization: formation of 1H-indenes and 1-alkylideneindans from arylboronate esters in aqueous media.

Authors:  Mark Lautens; Tzvetelina Marquardt
Journal:  J Org Chem       Date:  2004-07-09       Impact factor: 4.354

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  1 in total

1.  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

  1 in total

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