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Synthesis of alkenyl boronates from allyl-substituted aromatics using an olefin cross-metathesis protocol.
J Org Chem. 2013 Jul 05; 78(13):6786-92.JO

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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Publisher Full Text (DOI)

Authors+Show Affiliations

Hemelaere R
Sciences Chimiques de Rennes, UMR 6226 CNRS- Université de Rennes 1, 263, Avenue du Général Leclerc, Campus de Beaulieu, Bâtiment 10A, 35042 Rennes Cedex, France.
Carreaux F
No affiliation info available
Carboni B
No affiliation info available

MeSH

AlkenesBoronic AcidsCatalysisMolecular StructureOrganometallic CompoundsRuthenium

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23772914

Citation

Hemelaere, Rémy, et al. "Synthesis of Alkenyl Boronates From Allyl-substituted Aromatics Using an Olefin Cross-metathesis Protocol." The Journal of Organic Chemistry, vol. 78, no. 13, 2013, pp. 6786-92.
Hemelaere R, Carreaux F, Carboni B. Synthesis of alkenyl boronates from allyl-substituted aromatics using an olefin cross-metathesis protocol. J Org Chem. 2013;78(13):6786-92.
Hemelaere, R., Carreaux, F., & Carboni, B. (2013). Synthesis of alkenyl boronates from allyl-substituted aromatics using an olefin cross-metathesis protocol. The Journal of Organic Chemistry, 78(13), 6786-92. https://doi.org/10.1021/jo400872x
Hemelaere R, Carreaux F, Carboni B. Synthesis of Alkenyl Boronates From Allyl-substituted Aromatics Using an Olefin Cross-metathesis Protocol. J Org Chem. 2013 Jul 5;78(13):6786-92. PubMed PMID: 23772914.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of alkenyl boronates from allyl-substituted aromatics using an olefin cross-metathesis protocol. AU - Hemelaere,Rémy, AU - Carreaux,François, AU - Carboni,Bertrand, Y1 - 2013/06/24/ PY - 2013/6/19/entrez PY - 2013/6/19/pubmed PY - 2014/1/29/medline SP - 6786 EP - 92 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 13 N2 - 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. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23772914/Synthesis_of_alkenyl_boronates_from_allyl_substituted_aromatics_using_an_olefin_cross_metathesis_protocol_ L2 - https://doi.org/10.1021/jo400872x DB - PRIME DP - Unbound Medicine ER -