Ruthenium hydride catalyzed silylvinylation of terminal alkynes under ethylene atmosphere at 80 psi

The development of methods for the stereoselective synthesis of polysubstituted 1,3-dienes is a challenge to synthetic chemistry. Herein is reported a selective approach for the synthesis of polysubstituted 1,3-dienes using the ruthenium hydride catalyzed intramolecular silylvinylation of alkynes un...

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Bibliographic Details
Published inTetrahedron letters Vol. 58; no. 43; pp. 4054 - 4056
Main Authors Dixon, Alexandre D. C., Wilson, Robert J., Nguyen, Daniel D., Clark, Daniel A.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 25.10.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
CROSS-COUPLING REACTIONS
Oxasilacycle
Catalysis
INTERNAL ALKYNES
STEREOSELECTIVE-SYNTHESIS
Ruthenium hydride
Dienes
Silylvinylation
HIGHLY SUBSTITUTED 1,3-DIENES
ANTI-HYDROSILYLATION
TRANS-SILYLVINYLATION
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Summary:The development of methods for the stereoselective synthesis of polysubstituted 1,3-dienes is a challenge to synthetic chemistry. Herein is reported a selective approach for the synthesis of polysubstituted 1,3-dienes using the ruthenium hydride catalyzed intramolecular silylvinylation of alkynes under 80 psi of ethylene gas. This strategy affords a single diene isomer, is applicable to substrates with aryl and alkyl substitution at the propargyl and homopropargyl positions, and has been utilized in the synthesis of 5 and 6 -membered oxasilacycles. (C) 2017 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2017.09.023