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Regio- and stereoselective synthesis of conjugated trienes from silaborated 1,3-enynes
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
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2016 (English)In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 40, no 7, 6340-6346 p.Article in journal (Refereed) Published
Abstract [en]

Products obtained from palladium-catalyzed regioselective cis-addition of (chlorodimethylsilyl)pinacolborane to the alkyne bond of 1,4-disubstituted 1,3-enynes were subjected to Suzuki-Miyaura coupling with alkenyl iodides. Hiyama coupling of the resulting silanol-functionalized trienes provided tetrasubstituted conjugated trienes with different substitution patterns, whereas protiodesilylation with fluoride gave trisubstituted trienes. The methodology presented gives access to conjugated trienes with control of regio- and stereochemistry.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2016. Vol. 40, no 7, 6340-6346 p.
Keyword [en]
2 propanol, alkyne, boron, iodobenzene, palladium, silanol, silicon, trientine, Article, catalyst, chemical modification, column chromatography, desilylation, hydroboration, hydrosilylation, priority journal, protiodeboronation, protiodesilylation, proton nuclear magnetic resonance, purification, stereochemistry, Suzuki reaction, synthesis
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-195480DOI: 10.1039/c6nj01019aISI: 000385869600085ScopusID: 2-s2.0-84979022019OAI: oai:DiVA.org:kth-195480DiVA: diva2:1049818
Note

QC 20161125

Available from: 2016-11-25 Created: 2016-11-03 Last updated: 2016-11-25Bibliographically approved

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Li, EndeZhou, HuiÖstlund, VictorHertzberg, RobinMoberg, Christina
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