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Diversity-oriented synthesis of disubstituted alkenes using masked silanols.
Org Lett. 2010 Jun 18; 12(12):2806-9.OL

Abstract

The regio- and stereoselective synthesis and subsequent Hiyama cross coupling of pentafluorophenyldimethylvinylsilanes has been developed, thus providing a convenient and robust method for the diversity-oriented synthesis of (E)-, (Z)- and alpha-disubstituted alkenes from terminal alkynes. Pentafluorophenyldimethylvinylsilanes undergo cross-coupling reactions with excellent selectivity and in good yields, offering an attractive alternative to existing masked silanols.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Sore HF
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK CB2 1EW.
Blackwell DT
No affiliation info available
Macdonald SJ
No affiliation info available
Spring DR
No affiliation info available

MeSH

AlkenesAlkynesCatalysisCombinatorial Chemistry TechniquesHydrocarbons, FluorinatedMolecular StructureSilanesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20491504

Citation

Sore, Hannah F., et al. "Diversity-oriented Synthesis of Disubstituted Alkenes Using Masked Silanols." Organic Letters, vol. 12, no. 12, 2010, pp. 2806-9.
Sore HF, Blackwell DT, Macdonald SJ, et al. Diversity-oriented synthesis of disubstituted alkenes using masked silanols. Org Lett. 2010;12(12):2806-9.
Sore, H. F., Blackwell, D. T., Macdonald, S. J., & Spring, D. R. (2010). Diversity-oriented synthesis of disubstituted alkenes using masked silanols. Organic Letters, 12(12), 2806-9. https://doi.org/10.1021/ol100895d
Sore HF, et al. Diversity-oriented Synthesis of Disubstituted Alkenes Using Masked Silanols. Org Lett. 2010 Jun 18;12(12):2806-9. PubMed PMID: 20491504.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Diversity-oriented synthesis of disubstituted alkenes using masked silanols. AU - Sore,Hannah F, AU - Blackwell,David T, AU - Macdonald,Simon J F, AU - Spring,David R, PY - 2010/5/25/entrez PY - 2010/5/25/pubmed PY - 2010/9/8/medline SP - 2806 EP - 9 JF - Organic letters JO - Org Lett VL - 12 IS - 12 N2 - The regio- and stereoselective synthesis and subsequent Hiyama cross coupling of pentafluorophenyldimethylvinylsilanes has been developed, thus providing a convenient and robust method for the diversity-oriented synthesis of (E)-, (Z)- and alpha-disubstituted alkenes from terminal alkynes. Pentafluorophenyldimethylvinylsilanes undergo cross-coupling reactions with excellent selectivity and in good yields, offering an attractive alternative to existing masked silanols. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/20491504/Diversity_oriented_synthesis_of_disubstituted_alkenes_using_masked_silanols_ L2 - https://doi.org/10.1021/ol100895d DB - PRIME DP - Unbound Medicine ER -