Literature DB >> 16928076

Aryl trihydroxyborates: easily isolated discrete species convenient for direct application in coupling reactions.

Andrew N Cammidge1, Victoria H M Goddard, Hemant Gopee, Nicola L Harrison, David L Hughes, Christopher J Schubert, Benjamin M Sutton, Gary L Watts, Andrew J Whitehead.   

Abstract

A conceptually and practically simple alternative approach to the use of arylboron species as the organometallic component in cross-coupling processes is described whereby trihydroxyborate salts are isolated and directly employed. The protocol derives practical benefit from the ease and convenience of the isolation and subsequent use of the discrete borate salts, eliminates the need for additional base, and aids the use of correct reaction stoichiometry.

Entities:  

Year:  2006        PMID: 16928076     DOI: 10.1021/ol061564w

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


  10 in total

1.  Distinguishing between pathways for transmetalation in Suzuki-Miyaura reactions.

Authors:  Brad P Carrow; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-01-31       Impact factor: 15.419

2.  Structural, Kinetic, and Computational Characterization of the Elusive Arylpalladium(II)boronate Complexes in the Suzuki-Miyaura Reaction.

Authors:  Andy A Thomas; Hao Wang; Andrew F Zahrt; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2017-03-07       Impact factor: 15.419

3.  DNA Condensation with a Boron-Containing Cationic Peptide for Modeling Boron Neutron Capture Therapy.

Authors:  Chris C Perry; Jose Ramos-Méndez; Jamie R Milligan
Journal:  Radiat Phys Chem Oxf Engl 1993       Date:  2019-10-10       Impact factor: 2.858

4.  General method for synthesis of 2-heterocyclic N-methyliminodiacetic acid boronates.

Authors:  Graham R Dick; David M Knapp; Eric P Gillis; Martin D Burke
Journal:  Org Lett       Date:  2010-05-21       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

Review 6.  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

7.  A general solution for the 2-pyridyl problem.

Authors:  Graham R Dick; Eric M Woerly; Martin D Burke
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-27       Impact factor: 15.336

8.  Carbonylative Suzuki couplings of aryl bromides with boronic acid derivatives under base-free conditions.

Authors:  Klaus M Bjerglund; Troels Skrydstrup; Gary A Molander
Journal:  Org Lett       Date:  2014-03-17       Impact factor: 6.005

9.  Axial shielding of Pd(II) complexes enables perfect stereoretention in Suzuki-Miyaura cross-coupling of Csp3 boronic acids.

Authors:  Jonathan W Lehmann; Ian T Crouch; Daniel J Blair; Melanie Trobe; Pulin Wang; Junqi Li; Martin D Burke
Journal:  Nat Commun       Date:  2019-03-20       Impact factor: 14.919

10.  Oxidative Heck Reactions using Aryltrifluoroborates and Aryl N-Methyliminodiacetic Acid (MIDA) Boronates.

Authors:  Jonas Sävmarker; Jonas Lindh; Peter Nilsson; Per J R Sjöberg; Mats Larhed
Journal:  ChemistryOpen       Date:  2012-05-21       Impact factor: 2.911

  10 in total

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