Synthesis of functionalized vinyl boronates via ruthenium-catalyzed olefin cross-metathesis and subsequent conversion to vinyl halides

Journal of Organic Chemistry

Volumn 68, Issue 15, 2003, Pages 6031-6034

  Morrill, Christie ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLING REACTIONS;

CATALYST ACTIVITY; RUTHENIUM; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

OLEFINS;

1 PROPENYLPINACOL BORONIC ACID; ALKENE; BORONIC ACID DERIVATIVE; FUNCTIONAL GROUP; RUTHENIUM; UNCLASSIFIED DRUG; VINYL BROMIDE; VINYL DERIVATIVE; VINYL IODIDE; VINYLPINACOL BORONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL CONVERSION; CHEMICAL REACTION; CROSS METATHESIS; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

ALKENES; ANIONS; BORONIC ACIDS; CATALYSIS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; RUTHENIUM; VINYL COMPOUNDS;

EID: 0038034652     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0345345     Document Type: Article

References (34)

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26. The material that we isolated is a mixture of 4, its corresponding cyclic trimer, and probably small amounts of higher oligomers. The predominant species as detected by GC/MS is the cyclic trimer. In addition, the boronic acids in this mixture may be partially hydrated. Attempts to remove any excess water (using vacuum) from 4 after recrystallization resulted only in decomposition. However, the solid obtained after recrystallization was already of adequate purity to participate in cross-metathesis reactions, which work for both the monomeric and the trimeric versions of 4.
27. Efficient vinyl boronate cross-metathesis can also be achieved with use of catalyst 1 when unhindered aliphatic terminal olefins are used, as we have previously reported (ref 13).
28. Using excess cross partner rather than excess boronate did not significantly affect the amount of cross product formed.
29. Conversions were calculated relative to an anisole internal standard.
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31. Grubbs group, unpublished results.
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