Palladium-catalyzed intramolecular coupling between aryl iodides and allyl moieties via thermal and microwave-assisted conditions.

J Am Chem Soc

Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6.

Published: January 2005

AI Article Synopsis

  • Palladium-catalyzed reactions were developed for intramolecular cross-coupling of aryl iodides and allyl groups, using specific catalysts and conditions.
  • The method produced various trans-2,4-disubstituted 1,2,3,4-tetrahydroquinolines with high yields (73-88%) and strong diastereoselectivity.
  • This technique was also effective for creating a range of carbo- and heterocycles, including five- to seven-membered rings, using microwave-assisted methods.

Article Abstract

Palladium-catalyzed intramolecular cross-coupling reactions between aryl iodides and allyl moieties were successfully demonstrated in the presence of palladium catalyst, tri-o-tolylphosphine, a tertiary amine, and water. Several kinds of trans-2,4-disubstituted 1,2,3,4-tetrahydroquinolines were synthesized in 73-88% yields with excellent diastereoselectivities. This method was further applied to a large variety of substrates to form five-, six-, and seven-membered carbo- and heterocycles in good yields, regardless of the ring-containing atom, via microwave-assisted conditions.

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http://dx.doi.org/10.1021/ja043898rDOI Listing

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