Literature DB >> 21888362

Cross-coupling of mesylated phenol derivatives with potassium cyclopropyltrifluoroborate.

Gary A Molander1, Floriane Beaumard, Terren K Niethamer.   

Abstract

C-O activation of mesylates by a palladium catalyst and subsequent cross-coupling with potassium cyclopropyltrifluoroborate have been achieved with high yield. Both electron-enriched and electron-deficient aryl mesylates are suitable electrophilic partners for the Suzuki-Miyaura reaction. The scope was successfully extended to heteroaryl mesylates with yields up to 94%.

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Year:  2011        PMID: 21888362      PMCID: PMC3184376          DOI: 10.1021/jo2015246

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


  20 in total

Review 1.  Biosynthesis and metabolism of cyclopropane rings in natural compounds.

Authors:  Ludger A Wessjohann; Wolfgang Brandt; Thies Thiemann
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

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

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

4.  Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors:  Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2007-07       Impact factor: 60.622

5.  Ligand effects in bimetallic high oxidation state palladium systems.

Authors:  Alireza Ariafard; Christopher J T Hyland; Allan J Canty; Manab Sharma; Nigel J Brookes; Brian F Yates
Journal:  Inorg Chem       Date:  2010-11-02       Impact factor: 5.165

6.  Aryl trifluoroborates in Suzuki-Miyaura coupling: the roles of endogenous aryl boronic acid and fluoride.

Authors:  Mike Butters; Jeremy N Harvey; Jesus Jover; Alastair J J Lennox; Guy C Lloyd-Jones; Paul M Murray
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-12       Impact factor: 15.336

7.  A versatile catalyst system for Suzuki-Miyaura cross-coupling reactions of C(sp(2))-tosylates and mesylates.

Authors:  Brijesh Bhayana; Brett P Fors; Stephen L Buchwald
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

8.  Nickel-catalyzed C-O activation of phenol derivatives with potassium heteroaryltrifluoroborates.

Authors:  Gary A Molander; Floriane Beaumard
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

Review 9.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

10.  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

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  3 in total

1.  Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl mesylates.

Authors:  Gary A Molander; Inji Shin
Journal:  Org Lett       Date:  2012-05-31       Impact factor: 6.005

2.  Bright Side of Lignin Depolymerization: Toward New Platform Chemicals.

Authors:  Zhuohua Sun; Bálint Fridrich; Alessandra de Santi; Saravanakumar Elangovan; Katalin Barta
Journal:  Chem Rev       Date:  2018-01-16       Impact factor: 60.622

3.  Pd-catalyzed Suzuki-Miyaura cross-coupling reactions between sulfamates and potassium Boc-protected aminomethyltrifluoroborates.

Authors:  Gary A Molander; Inji Shin
Journal:  Org Lett       Date:  2013-05-06       Impact factor: 6.005

  3 in total

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