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A new regioselective Heck vinylation with enamides. Synthesis and investigation of fluorous-tagged bidentate ligands for fast separation
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2003 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 68, no 17, 6639-6645 p.Article in journal (Refereed) PublishedText
Abstract [en]

Internal ligand-controlled Heck vinylations of enamides were performed with high regioselectivity and delivered moderate to good yields of dienamides. Controlled heating by microwave irradiation accelerated the palladium-catalyzed reactions, and full conversions were achieved after reaction times of only 15-30 min. New bidentate fluorous-tagged 1,3-bis(diphenylphosphino)propane ligands (F-dppp's) were synthesized and examined. The cationic vinylations of the enamides with F-dppp ligands rendered essentially the same alpha-selectivity and catalytic activity as in those vinylations where nonfluorous ligands were employed. After reaction, the fluorous-tagged ligand material was easily removed by convenient solid fluorous phase separation. The high selectivity, simplicity, and generality of the experimental procedure should make this approach to 2-acylamino-1,3-butadienes attractive.

Place, publisher, year, edition, pages
Uppsala Univ, BMC, Dept Organ Pharmaceut Chem, SE-75123 Uppsala, Sweden. Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA., 2003. Vol. 68, no 17, 6639-6645 p.
National Category
Organic Chemistry
URN: urn:nbn:se:uu:diva-275406DOI: 10.1021/jo034265iISI: 000184833500023PubMedID: 12919028OAI: oai:DiVA.org:uu-275406DiVA: diva2:900293
Available from: 2016-02-03 Created: 2016-02-03 Last updated: 2016-02-03

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