Literature DB >> 18266374

General method for the expedient synthesis of salt-free diorganozinc reagents using zinc methoxide.

Alexandre Côté1, André B Charette.   

Abstract

The effect of counterions has a great impact on the solubility of magnesium salts in Et2O. By reacting Zn(OMe)2 with readily available Grignard reagents, it was possible to induce the complete precipitation of magnesium salts and then obtain salt-free diorganozinc reagents after centrifugation/filtration. This practical method to generate dialkylzinc reagents as well as mixed diorganozinc reagents was successfully tested in various catalytic enantioselective reactions, proving the purity of the product and its synthetic usefulness.

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Year:  2008        PMID： 18266374     DOI： 10.1021/ja710864p

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  6 in total

1.  Synthesis of 5-fluoroalkylated pyrimidine nucleosides via Negishi cross-coupling.

Authors:  Ann-Marie Chacko; Wenchao Qu; Hank F Kung
Journal:  J Org Chem       Date:  2008-06-04       Impact factor: 4.354

2.  Catalytic asymmetric synthesis of secondary nitriles via stereoconvergent Negishi arylations and alkenylations of racemic α-bromonitriles.

Authors:  Junwon Choi; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2012-05-21       Impact factor: 15.419

3.  Facially selective Cu-catalyzed carbozincation of cyclopropenes using arylzinc reagents formed by sequential I/Mg/Zn exchange.

Authors:  Vinod Tarwade; Ramajeyam Selvaraj; Joseph M Fox
Journal:  J Org Chem       Date:  2012-10-19       Impact factor: 4.354

4.  Continuous flow enantioselective arylation of aldehydes with ArZnEt using triarylboroxins as the ultimate source of aryl groups.

Authors:  Julien Rolland; Xacobe C Cambeiro; Carles Rodríguez-Escrich; Miquel A Pericàs
Journal:  Beilstein J Org Chem       Date:  2009-10-15       Impact factor: 2.883

5.  Practical catalytic asymmetric synthesis of diaryl-, aryl heteroaryl-, and diheteroarylmethanols.

Authors:  Luca Salvi; Jeung Gon Kim; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2009-09-02       Impact factor: 15.419

6.  Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes To Form Hindered Secondary Alcohols.

Authors:  Kevin J Garcia; Michael M Gilbert; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2019-01-29       Impact factor: 15.419
  6 in total

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