Literature DB >> 18196177

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

Gary A Molander, Jungyeob Ham, Dave G Seapy.   

Abstract

The Suzuki-Miyaura-type cross-coupling reaction of potassium alkyltrifluoroborates with various alkenyl bromides in the presence of 10 mol % of PdCl(2)(dppf)·CH(2)Cl(2) and 3.0 equiv of Cs(2)CO(3) in aqueous toluene at 80 °C provided the desired compounds in 49-95% yields. A variety of functional groups in the potassium alkyltrifluoroborates were tolerated under the basic conditions.

Entities:  

Year:  2007        PMID： 18196177      PMCID： PMC1827200          DOI： 10.1016/j.tet.2006.10.088

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


  17 in total

1.  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

2.  Palladium(0)-catalyzed suzuki-miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates with alkenyl bromides.

Authors:  Gary A Molander; Tiziano Fumagalli
Journal:  J Org Chem       Date:  2006-07-21       Impact factor: 4.354

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.  Stereoselective Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates with alkenyl bromides.

Authors:  Gary A Molander; Luciana A Felix
Journal:  J Org Chem       Date:  2005-05-13       Impact factor: 4.354

8.  Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates.

Authors:  Gary A Molander; Carmem R Bernardi
Journal:  J Org Chem       Date:  2002-11-29       Impact factor: 4.354

9.  Palladium(0)-catalyzed synthesis of chiral ene-allenes using alkenyl trifluoroborates.

Authors:  Gary A Molander; Erin M Sommers; Sharon R Baker
Journal:  J Org Chem       Date:  2006-02-17       Impact factor: 4.354

10.  One-pot synthesis of trisubstituted conjugated dienes via sequential Suzuki-Miyaura cross-coupling with alkenyl- and alkyltrifluoroborates.

Authors:  Gary A Molander; Yasuo Yokoyama
Journal:  J Org Chem       Date:  2006-03-17       Impact factor: 4.354
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  2 in total

1.  Facile synthesis of highly functionalized ethyltrifluoroborates.

Authors:  Gary A Molander; Wilma Febo-Ayala; Montserrat Ortega-Guerra
Journal:  J Org Chem       Date:  2008-06-28       Impact factor: 4.354

Review 2.  Potassium trifluoroborate salts as convenient, stable reagents for difficult alkyl transfers.

Authors:  Gary A Molander; Deidre L Sandrock
Journal:  Curr Opin Drug Discov Devel       Date:  2009-11
  2 in total

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