Literature DB >> 26973991

Copper-catalyzed cross-coupling reactions of epoxides with gem-diborylmethane: access to γ-hydroxyl boronic esters.

Ahmed Ebrahim-Alkhalil1, Zhen-Qi Zhang, Tian-Jun Gong, Wei Su, Xiao-Yu Lu, Bin Xiao, Yao Fu.   

Abstract

Herein, we describe a novel copper-catalyzed epoxide opening reaction with gem-diborylmethane. Aliphatic, aromatic epoxides as well as aziridines are converted to the corresponding γ-pinacolboronate alcohols or amines in moderate to excellent yields. This new reaction provides beneficial applications for classic epoxide substrates as well as interesting gem-diborylalkane reagents.

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Year:  2016        PMID: 26973991     DOI: 10.1039/c5cc09817c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  4 in total

1.  A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.

Authors:  Xun Liu; T Maxwell Deaton; Fredrik Haeffner; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-09       Impact factor: 15.336

2.  Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones.

Authors:  Michael Z Liang; Simon J Meek
Journal:  J Am Chem Soc       Date:  2020-05-18       Impact factor: 15.419

3.  Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane.

Authors:  Stephanie A Murray; Michael Z Liang; Simon J Meek
Journal:  J Am Chem Soc       Date:  2017-09-27       Impact factor: 15.419

4.  Cu-Catalyzed Cross-Coupling of Benzylboronic Esters and Epoxides.

Authors:  Sophia G Gierszal; Timothy J Barker
Journal:  Tetrahedron Lett       Date:  2021-09-07       Impact factor: 2.032

  4 in total

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