Regio- and stereoselective synthesis of conjugated trienes from silaborated 1,3-enynes
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
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.
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
IdentifiersURN: urn:nbn:se:kth:diva-195480DOI: 10.1039/c6nj01019aISI: 000385869600085ScopusID: 2-s2.0-84979022019OAI: oai:DiVA.org:kth-195480DiVA: diva2:1049818
QC 201611252016-11-252016-11-032016-11-25Bibliographically approved