Highly regioselective, sequential, and multiple palladium-catalyzed arylations of vinyl ethers carrying a coordinating auxiliary: An example of a Heck triarylation process
2001 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 123, no 34, 8217-8225 p.Article in journal (Refereed) PublishedText
This article describes the development of new auxiliary-accelerated Heck multiarylations by intramolecular presentation of the oxidative addition complex. The introduction of a specific, palladium-coordinating dimethylamino group allows for the desired chelation-accelerated and chelation-controlled triand diarylation reactions. We report (a) the first example of a Heck triarylation process, (b) highly selective palladium-catalyzed diarylations of alkyl vinyl ethers, and (c) a very rapid two-phase protocol for the microwave-assisted hydrolysis of amino-substituted, arylated vinyl ethers constituting an entry to diarylated ethanals and substituted desoxybenzoins. X-ray structures and product patterns support the suggested substrate-controlled Heck reaction pathway. The catalyst-directing alkyl dimethylamino functionality was rapidly (1-2 min) and efficiently released by microwave hydrolysis after Heck multiarylation reactions. The liberated aromatic carbonyl compounds were thereafter isolated and fully characterized.
Place, publisher, year, edition, pages
Uppsala Univ, Uppsala Biomed Ctr, Dept Organ Pharmaceut Chem, SE-75123 Uppsala, Sweden., 2001. Vol. 123, no 34, 8217-8225 p.
IdentifiersURN: urn:nbn:se:uu:diva-275422DOI: 10.1021/ja011019kISI: 000170730000007PubMedID: 11516272OAI: oai:DiVA.org:uu-275422DiVA: diva2:900264