Palladium-catalyzed intramolecular coupling reactions between aryl and vinyl iodides and allylic moieties.
Contributors: University of Toronto.  Dept. of Chemistry.
Published: 2007
Language: eng
Number of pages: 71
ISBN-13: 9780494274385
Description: The effect of changing the allylic group in a palladium-catalyzed direct cross-coupling between aryl halides and allylic moieties was examined. beta-Heteroatom elimination was found to preferentially occur over beta-hydride elimination for substrates possessing an allylic moiety containing a good leaving group. Extension of the reaction conditions to the intramolecular coupling of aryl iodides and allylic alcohols allows for the rapid synthesis of a variety of carbo- and herterocycles containing aldehyde functionalities in good to excellent yields. Optimization of the palladium-catalyzed cross-coupling reaction between a vinyl halide and allyl carbonate allowed for the efficient synthesis of six-membered nitrogen-containing cycles. The nature of the leaving group strongly influences the yield of the coupling reaction. Application of the optimized conditions to the intramolecular cyclization of a vinyl iodide and allylic alcohol indicates the utility of this methodology in the formation of carbonyl-containing heterocycles.
Notes: Source: Masters Abstracts International, Volume: 45-06, page: 3164.

Thesis (M.Sc.)--University of Toronto, 2007.

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