Chelation-Mediated Palladium(II)-Catalyzed Domino Heck-Mizoroki/Suzuki-Miyaura Reactions Using Arylboronic Acids: Increasing Scope and Mechanistic Understanding
2011 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 76, no 8, 2433-2438 p.Article in journal (Refereed) Published
A palladium(II)-catalyzed Heck-Mizoroki/Suzuki-Miyaura domino reaction involving metal coordinating dimethylaminoethyl vinyl ethers and a number of electron-rich and electron-deficient arylboronic acids has been developed. Through variation of the temperature and the concentration of the p-benzoquinone (p-Bq) ligand/reoxidant, conditions for the robust and convenient one-pot generation of diarylated-saturated ethers were identified. With the aid of coordination of the dimethylamino group to the arylpalladium intermediate, the otherwise predominant formation of the beta-arylated olefin could be reversed. A reaction route involving a chelation-controlled carbopalladation, providing a p-Bq stabilized six-membered palladacycle, followed by transmetalation and reductive elimination is suggested to explain the selective formation of saturated diarylated ether products.
Place, publisher, year, edition, pages
2011. Vol. 76, no 8, 2433-2438 p.
IdentifiersURN: urn:nbn:se:uu:diva-152784DOI: 10.1021/jo1018188ISI: 000289187300004PubMedID: 21417443OAI: oai:DiVA.org:uu-152784DiVA: diva2:414075