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Ruthenium-catalyzed [2 + 2] cycloadditions of bicyclic alkenes with alkynyl phosphonates.
J Org Chem. 2009 Aug 07; 74(15):5762-5.JO

Abstract

Ruthenium-catalyzed [2 + 2] cycloadditions of bicyclic alkenes with alkynyl phosphonates were investigated. The phosphonate moieties were found to be compatible with the Ru-catalyzed cycloadditions giving the corresponding cyclobutene cycloadducts in low to excellent yield (up to 96%). Alkynyl phosphonates showed lower reactivity than other heteroatom-substituted alkynes such as alkynyl halides, ynamides, alkynyl sulfides, and alkynyl sulfones and required a higher reaction temperature and much longer reaction time.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Cockburn N
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario N1G 2W1, Canada.
Karimi E
No affiliation info available
Tam W
No affiliation info available

MeSH

AlkenesAlkynesCatalysisCyclizationMolecular StructureOrganometallic CompoundsOrganophosphonatesRutheniumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19572573

Citation

Cockburn, Neil, et al. "Ruthenium-catalyzed [2 + 2] Cycloadditions of Bicyclic Alkenes With Alkynyl Phosphonates." The Journal of Organic Chemistry, vol. 74, no. 15, 2009, pp. 5762-5.
Cockburn N, Karimi E, Tam W. Ruthenium-catalyzed [2 + 2] cycloadditions of bicyclic alkenes with alkynyl phosphonates. J Org Chem. 2009;74(15):5762-5.
Cockburn, N., Karimi, E., & Tam, W. (2009). Ruthenium-catalyzed [2 + 2] cycloadditions of bicyclic alkenes with alkynyl phosphonates. The Journal of Organic Chemistry, 74(15), 5762-5. https://doi.org/10.1021/jo9010206
Cockburn N, Karimi E, Tam W. Ruthenium-catalyzed [2 + 2] Cycloadditions of Bicyclic Alkenes With Alkynyl Phosphonates. J Org Chem. 2009 Aug 7;74(15):5762-5. PubMed PMID: 19572573.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Ruthenium-catalyzed [2 + 2] cycloadditions of bicyclic alkenes with alkynyl phosphonates. AU - Cockburn,Neil, AU - Karimi,Elham, AU - Tam,William, PY - 2009/7/4/entrez PY - 2009/7/4/pubmed PY - 2009/12/16/medline SP - 5762 EP - 5 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 15 N2 - Ruthenium-catalyzed [2 + 2] cycloadditions of bicyclic alkenes with alkynyl phosphonates were investigated. The phosphonate moieties were found to be compatible with the Ru-catalyzed cycloadditions giving the corresponding cyclobutene cycloadducts in low to excellent yield (up to 96%). Alkynyl phosphonates showed lower reactivity than other heteroatom-substituted alkynes such as alkynyl halides, ynamides, alkynyl sulfides, and alkynyl sulfones and required a higher reaction temperature and much longer reaction time. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19572573/Ruthenium_catalyzed_[2_+_2]_cycloadditions_of_bicyclic_alkenes_with_alkynyl_phosphonates_ L2 - https://doi.org/10.1021/jo9010206 DB - PRIME DP - Unbound Medicine ER -