Literature DB >> 33585070

Potassium Trimethylsilanolate Enables Rapid, Homogeneous Suzuki-Miyaura Cross-Coupling of Boronic Esters.

Connor P Delaney1, Vincent M Kassel1, Scott E Denmark1.   

Abstract

Herein, a mild and operationally simple method for the Suzuki-Miyaura cross-coupling of boronic esters is described. Central to this advance is the use of the organic-soluble base, potassium trimethylsilanolate, which allows for a homogeneous, anhydrous cross-coupling. The coupling proceeds at a rapid rate, often furnishing products in quantitative yield in less than 5 min. By applying this method, a >10-fold decrease in reaction time was observed for three published reactions which required >48 h to reach satisfactory conversion.

Entities:  

Keywords:  Suzuki–Miyaura reaction; cross-coupling; homogeneous catalysis; palladium; synthetic methods

Year:  2019        PMID： 33585070      PMCID： PMC7880502          DOI： 10.1021/acscatal.9b04353

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.084


  29 in total

1.  Design, validation, and implementation of a rapid-injection NMR system.

Authors:  Scott E Denmark; Bruce J Williams; Brian M Eklov; Son M Pham; Gregory L Beutner
Journal:  J Org Chem       Date:  2010-08-20       Impact factor: 4.354

2.  Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize.

Authors:  Carin C C Johansson Seechurn; Matthew O Kitching; Thomas J Colacot; Victor Snieckus
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-09       Impact factor: 15.336

3.  Base-Catalyzed Aryl-B(OH)2 Protodeboronation Revisited: From Concerted Proton Transfer to Liberation of a Transient Aryl Anion.

Authors:  Paul A Cox; Marc Reid; Andrew G Leach; Andrew D Campbell; Edward J King; Guy C Lloyd-Jones
Journal:  J Am Chem Soc       Date:  2017-09-11       Impact factor: 15.419

4.  Comparison of arylboron-based nucleophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling with aryl mesylates and sulfamates.

Authors:  Na Zhang; David J Hoffman; Nicholas Gutsche; Jayesh Gupta; Virgil Percec
Journal:  J Org Chem       Date:  2012-06-29       Impact factor: 4.354

5.  Elucidating the Role of the Boronic Esters in the Suzuki-Miyaura Reaction: Structural, Kinetic, and Computational Investigations.

Authors:  Andy A Thomas; Andrew F Zahrt; Connor P Delaney; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2018-03-15       Impact factor: 15.419

6.  Copper-facilitated Suzuki reactions: application to 2-heterocyclic boronates.

Authors:  James Z Deng; Daniel V Paone; Anthony T Ginnetti; Hideki Kurihara; Spencer D Dreher; Steven A Weissman; Shaun R Stauffer; Christopher S Burgey
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

7.  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

8.  Copper-catalyzed Suzuki-Miyaura coupling of arylboronate esters: transmetalation with (PN)CuF and identification of intermediates.

Authors:  Santosh K Gurung; Surendra Thapa; Arjun Kafle; Diane A Dickie; Ramesh Giri
Journal:  Org Lett       Date:  2014-02-05       Impact factor: 6.005

9.  Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis.

Authors:  Gereon Altenhoff; Richard Goddard; Christian W Lehmann; Frank Glorius
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

10.  Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki-Miyaura Cross Coupling with Electron-Poor Substrates.

Authors:  David Bulfield; Stefan M Huber
Journal:  J Org Chem       Date:  2017-12-04       Impact factor: 4.354
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  3 in total

1.  Potassium Trimethylsilanolate-Promoted, Anhydrous Suzuki-Miyaura Cross-Coupling Reaction Proceeds via the "Boronate Mechanism": Evidence for the Alternative Fork in the Trail.

Authors:  Connor P Delaney; Daniel P Marron; Alexander S Shved; Richard N Zare; Robert M Waymouth; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2022-03-01       Impact factor: 15.419

2.  Heteroaryl-Heteroaryl, Suzuki-Miyaura, Anhydrous Cross-Coupling Reactions Enabled by Trimethyl Borate.

Authors:  Vincent M Kassel; Christopher M Hanneman; Connor P Delaney; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2021-08-20       Impact factor: 16.383

3.  Synthesis and Antibacterial Activity Evaluation of Biphenyl and Dibenzofuran Derivatives as Potential Antimicrobial Agents against Antibiotic-Resistant Bacteria.

Authors:  Xing Wang; Hao-Yu Fu; Wei He; Yu-Ting Xiang; Ze-Cheng Yang; Yi Kuang; Sheng-Xiang Yang
Journal:  Curr Issues Mol Biol       Date:  2022-09-07       Impact factor: 2.976
  3 in total

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