Literature DB >> 18588349

Facile synthesis of highly functionalized ethyltrifluoroborates.

Gary A Molander1, Wilma Febo-Ayala, Montserrat Ortega-Guerra.   

Abstract

Organotrifluoroborates are generating increased interest because of their ease of preparation and purification and indefinite shelf life. Herein we report the preparation of organotrifluoroborates bearing functional groups that can be manipulated at different stages of the synthetic route, exploiting the inertness of their carbon-boron bonds. The alkylation of 2,2-dicyanoethyltrifluoroborate with a variety of electrophiles and of (EWG)2CH2 with potassium iodomethyltrifluoroborate resulted in di- and trisubstituted ethyltrifluoroborates in good to excellent yields.

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Year:  2008        PMID: 18588349      PMCID: PMC2504466          DOI: 10.1021/jo800760f

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  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.  Cross-coupling reactions of potassium alkyltrifluoroborates with aryl and 1-alkenyl trifluoromethanesulfonates.

Authors:  G A Molander; T Ito
Journal:  Org Lett       Date:  2001-02-08       Impact factor: 6.005

4.  Synthesis of functionalized organotrifluoroborates via halomethyltrifluoroborates.

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

5.  Expanding organoboron chemistry: epoxidation of potassium organotrifluoroborates.

Authors:  Gary A Molander; María Ribagorda
Journal:  J Am Chem Soc       Date:  2003-09-17       Impact factor: 15.419

6.  B-alkyl suzuki-miyaura cross-coupling reactions with air-stable potassium alkyltrifluoroborates.

Authors:  Gary A Molander; Chang-Soo Yun; María Ribagorda; Betina Biolatto
Journal:  J Org Chem       Date:  2003-07-11       Impact factor: 4.354

7.  Asymmetric alkyldifluoroboranes and their use in secondary amine synthesis.

Authors:  Donald S Matteson; Gyung Youn Kim
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

8.  Palladium-catalyzed cross-coupling reaction of alkenyl bromides with potassium alkyltrifluoroborates.

Authors:  Gary A Molander; Jungyeob Ham; Dave G Seapy
Journal:  Tetrahedron       Date:  2007-01-15       Impact factor: 2.457

9.  A study of the effect on nucleophilic hydrolytic activity of pancreatic elastase, trypsin, chymotrypsin, and leucine aminopeptidase by boronic acids in the presence of arabinogalactan: a subsequent study on the hydrolytic activity of chymotrypsin by boronic acids in the presence of mono-, di-, and trisaccharides.

Authors:  Reem Smoum; Abraham Rubinstein; Morris Srebnik
Journal:  Bioorg Chem       Date:  2003-12       Impact factor: 5.275

  9 in total
  3 in total

1.  Metal-free chlorodeboronation of organotrifluoroborates.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2011-08-03       Impact factor: 4.354

2.  Oxidation of organotrifluoroborates via oxone.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2010-12-30       Impact factor: 4.354

3.  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

  3 in total

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