Literature DB >> 23772914

Synthesis of alkenyl boronates from allyl-substituted aromatics using an olefin cross-metathesis protocol.

Rémy Hemelaere1, François Carreaux, Bertrand Carboni.   

Abstract

An efficient synthesis of 3-aryl-1-propenyl boronates from pinacol vinyl boronic ester and allyl-substituted aromatics by cross metathesis is reported. Although the allylbenzene derivatives are prone to isomerization reaction under metathesis conditions, we found that some ruthenium catalysts are effective for this methodology. This strategy thus provides an interesting alternative approach to alkyne hydroboration, leading to the preparation of unknown compounds. Moreover, the boron substituent can be replaced by various functional groups in good yields.

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Year:  2013        PMID: 23772914     DOI: 10.1021/jo400872x

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  7 in total

1.  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

2.  Enantiomerically enriched tris(boronates): readily accessible conjunctive reagents for asymmetric synthesis.

Authors:  John R Coombs; Liang Zhang; James P Morken
Journal:  J Am Chem Soc       Date:  2014-11-11       Impact factor: 15.419

3.  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

4.  Optimized Ring Closing Metathesis Reaction Conditions To Suppress Desallyl Side Products in the Solid-Phase Synthesis of Cyclic Peptides Involving Tyrosine(O-allyl).

Authors:  Solomon A Gisemba; Jane V Aldrich
Journal:  J Org Chem       Date:  2020-01-13       Impact factor: 4.354

5.  Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins.

Authors:  Brendan L Quigley; Robert H Grubbs
Journal:  Chem Sci       Date:  2014-02       Impact factor: 9.825

6.  Vinylboronic Acids as Fast Reacting, Synthetically Accessible, and Stable Bioorthogonal Reactants in the Carboni-Lindsey Reaction.

Authors:  Selma Eising; Francis Lelivelt; Kimberly M Bonger
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-08       Impact factor: 15.336

Review 7.  Synergistic approach to polycycles through Suzuki-Miyaura cross coupling and metathesis as key steps.

Authors:  Sambasivarao Kotha; Milind Meshram; Chandravathi Chakkapalli
Journal:  Beilstein J Org Chem       Date:  2018-09-21       Impact factor: 2.883

  7 in total

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