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Stereocontrolled Synthesis of Vinyl Boronates and Vinyl Silanes via Atom-Economical Ruthenium-Catalyzed Alkene-Alkyne Coupling.
Angew Chem Int Ed Engl. 2015 Dec 21; 54(52):15863-6.AC

Abstract

The synthesis of vinyl boronates and vinyl silanes was achieved by employing a Ru-catalyzed alkene-alkyne coupling reaction of allyl boronates or allyl silanes with various alkynes. The double bond geometry in the generated vinyl boronates can be remotely controlled by the juxtaposing boron- and silicon groups on the alkyne substrate. The synthetic utility of the coupling products has been demonstrated in a variety of synthetic transformations, including iterative cross-coupling reactions, and a Chan-Lam-type allyloxylation followed by a Claisen rearrangement. A sequential one-pot alkene-alkyne-coupling/allylation-sequence with an aldehyde to deliver a highly complex α-silyl-β-hydroxy olefin with a handle for further functionalization was also realized.

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Authors+Show Affiliations

Trost BM
Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA). bmtrost@stanford.edu.
Koester DC
Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA).
Herron AN
Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA).

MeSH

AlkenesAlkynesBoronic AcidsCatalysisRutheniumVinyl Compounds

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

26572804

Citation

Trost, Barry M., et al. "Stereocontrolled Synthesis of Vinyl Boronates and Vinyl Silanes Via Atom-Economical Ruthenium-Catalyzed Alkene-Alkyne Coupling." Angewandte Chemie (International Ed. in English), vol. 54, no. 52, 2015, pp. 15863-6.
Trost BM, Koester DC, Herron AN. Stereocontrolled Synthesis of Vinyl Boronates and Vinyl Silanes via Atom-Economical Ruthenium-Catalyzed Alkene-Alkyne Coupling. Angew Chem Int Ed Engl. 2015;54(52):15863-6.
Trost, B. M., Koester, D. C., & Herron, A. N. (2015). Stereocontrolled Synthesis of Vinyl Boronates and Vinyl Silanes via Atom-Economical Ruthenium-Catalyzed Alkene-Alkyne Coupling. Angewandte Chemie (International Ed. in English), 54(52), 15863-6. https://doi.org/10.1002/anie.201509238
Trost BM, Koester DC, Herron AN. Stereocontrolled Synthesis of Vinyl Boronates and Vinyl Silanes Via Atom-Economical Ruthenium-Catalyzed Alkene-Alkyne Coupling. Angew Chem Int Ed Engl. 2015 Dec 21;54(52):15863-6. PubMed PMID: 26572804.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereocontrolled Synthesis of Vinyl Boronates and Vinyl Silanes via Atom-Economical Ruthenium-Catalyzed Alkene-Alkyne Coupling. AU - Trost,Barry M, AU - Koester,Dennis C, AU - Herron,Alastair N, Y1 - 2015/11/17/ PY - 2015/10/02/received PY - 2015/11/18/entrez PY - 2015/11/18/pubmed PY - 2016/10/1/medline KW - atom economy KW - boron KW - cross-coupling KW - homogeneous catalysis KW - ruthenium SP - 15863 EP - 6 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 54 IS - 52 N2 - The synthesis of vinyl boronates and vinyl silanes was achieved by employing a Ru-catalyzed alkene-alkyne coupling reaction of allyl boronates or allyl silanes with various alkynes. The double bond geometry in the generated vinyl boronates can be remotely controlled by the juxtaposing boron- and silicon groups on the alkyne substrate. The synthetic utility of the coupling products has been demonstrated in a variety of synthetic transformations, including iterative cross-coupling reactions, and a Chan-Lam-type allyloxylation followed by a Claisen rearrangement. A sequential one-pot alkene-alkyne-coupling/allylation-sequence with an aldehyde to deliver a highly complex α-silyl-β-hydroxy olefin with a handle for further functionalization was also realized. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/26572804/Stereocontrolled_Synthesis_of_Vinyl_Boronates_and_Vinyl_Silanes_via_Atom_Economical_Ruthenium_Catalyzed_Alkene_Alkyne_Coupling_ DB - PRIME DP - Unbound Medicine ER -