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Ruthenium-catalyzed ortho-alkenylation of phenylphosphine oxides through regio- and stereoselective alkyne insertion into C-H bonds.
J Org Chem. 2013 Aug 16; 78(16):8098-104.JO

Abstract

Direct ortho-substitution took place efficiently upon treatment of tri-, di-, and monoarylphosphine oxides with internal alkynes in the presence of a ruthenium catalyst to produce (o-alkenylphenyl)phosphine oxides regio- and stereoselectively. Chemoselective reduction of a product gave the corresponding (o-alkenylphenyl)phosphine, which may be useful as a ligand for transition metals.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Itoh M
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Hashimoto Y
No affiliation info available
Hirano K
No affiliation info available
Satoh T
No affiliation info available
Miura M
No affiliation info available

MeSH

AlkynesCatalysisMolecular StructureOrganometallic CompoundsOxidesPhosphinesRutheniumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23883373

Citation

Itoh, Masaki, et al. "Ruthenium-catalyzed Ortho-alkenylation of Phenylphosphine Oxides Through Regio- and Stereoselective Alkyne Insertion Into C-H Bonds." The Journal of Organic Chemistry, vol. 78, no. 16, 2013, pp. 8098-104.
Itoh M, Hashimoto Y, Hirano K, et al. Ruthenium-catalyzed ortho-alkenylation of phenylphosphine oxides through regio- and stereoselective alkyne insertion into C-H bonds. J Org Chem. 2013;78(16):8098-104.
Itoh, M., Hashimoto, Y., Hirano, K., Satoh, T., & Miura, M. (2013). Ruthenium-catalyzed ortho-alkenylation of phenylphosphine oxides through regio- and stereoselective alkyne insertion into C-H bonds. The Journal of Organic Chemistry, 78(16), 8098-104. https://doi.org/10.1021/jo401393b
Itoh M, et al. Ruthenium-catalyzed Ortho-alkenylation of Phenylphosphine Oxides Through Regio- and Stereoselective Alkyne Insertion Into C-H Bonds. J Org Chem. 2013 Aug 16;78(16):8098-104. PubMed PMID: 23883373.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Ruthenium-catalyzed ortho-alkenylation of phenylphosphine oxides through regio- and stereoselective alkyne insertion into C-H bonds. AU - Itoh,Masaki, AU - Hashimoto,Yuto, AU - Hirano,Koji, AU - Satoh,Tetsuya, AU - Miura,Masahiro, Y1 - 2013/08/06/ PY - 2013/7/26/entrez PY - 2013/7/26/pubmed PY - 2013/12/18/medline SP - 8098 EP - 104 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 16 N2 - Direct ortho-substitution took place efficiently upon treatment of tri-, di-, and monoarylphosphine oxides with internal alkynes in the presence of a ruthenium catalyst to produce (o-alkenylphenyl)phosphine oxides regio- and stereoselectively. Chemoselective reduction of a product gave the corresponding (o-alkenylphenyl)phosphine, which may be useful as a ligand for transition metals. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23883373/Ruthenium_catalyzed_ortho_alkenylation_of_phenylphosphine_oxides_through_regio__and_stereoselective_alkyne_insertion_into_C_H_bonds_ L2 - https://doi.org/10.1021/jo401393b DB - PRIME DP - Unbound Medicine ER -