Literature DB >> 20067245

Copper-promoted coupling of vinyl boronates and alcohols: a mild synthesis of allyl vinyl ethers.

Ryan E Shade1, Alan M Hyde, John-Carl Olsen, Craig A Merlic.   

Abstract

A copper-promoted coupling of vinyl pinacol boronate esters and alcohols for the synthesis of enol ethers is reported. The reaction occurs in 50-99% yield and is compatible with a variety of functional groups. Cupric acetate is the copper source, and triethylamine buffer is used to prevent protodeboration; the reaction occurs at room temperature. In addition to excellent chemoselectivity, the reaction is stereospecific.

Entities:  

Year:  2010        PMID： 20067245     DOI： 10.1021/ja907982w

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


  14 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Direct Synthesis of Alkenyl Boronic Esters from Unfunctionalized Alkenes: A Boryl-Heck Reaction.

Authors:  William B Reid; Jesse J Spillane; Sarah B Krause; Donald A Watson
Journal:  J Am Chem Soc       Date:  2016-04-22       Impact factor: 15.419

3.  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

4.  Nickel-Catalyzed Intramolecular C-O Bond Formation: Synthesis of Cyclic Enol Ethers.

Authors:  Seo-Jung Han; Ryohei Doi; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-09       Impact factor: 15.336

5.  Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters.

Authors:  Barbara J Casavant; Zainab M Khoder; Ilyas A Berhane; Sherry R Chemler
Journal:  Org Lett       Date:  2015-12-01       Impact factor: 6.005

6.  Evidence for alkene cis-aminocupration, an aminooxygenation case study: kinetics, EPR spectroscopy, and DFT calculations.

Authors:  Monissa C Paderes; Lee Belding; Branden Fanovic; Travis Dudding; Jerome B Keister; Sherry R Chemler
Journal:  Chemistry       Date:  2012-01-11       Impact factor: 5.236

7.  Synthesis of vinyl boronates from aldehydes by a practical boron-Wittig reaction.

Authors:  John R Coombs; Liang Zhang; James P Morken
Journal:  Org Lett       Date:  2015-03-23       Impact factor: 6.005

8.  Synthesis of Trisubstituted Alkenyl Boronic Esters from Alkenes Using the Boryl-Heck Reaction.

Authors:  William B Reid; Donald A Watson
Journal:  Org Lett       Date:  2018-10-16       Impact factor: 6.005

9.  Stereocontrolled Synthesis of Vinyl Boronates and Vinyl Silanes via Atom-Economical Ruthenium-Catalyzed Alkene-Alkyne Coupling.

Authors:  Barry M Trost; Dennis C Koester; Alastair N Herron
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-17       Impact factor: 15.336

10.  Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C-H Borylation.

Authors:  Yu Feng; Dane Holte; Jochen Zoller; Shigenobu Umemiya; Leah R Simke; Phil S Baran
Journal:  J Am Chem Soc       Date:  2015-08-11       Impact factor: 15.419
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