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Izmir Institute of Technology

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Browsing Izmir Institute of Technology by Subject "1,3-Substitution reactions"

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    Master Thesis
    Synthesis of allyl alcohols by paladium-catalyzed 1,3-substitution reactions of alkenyl epoxides with organoborons
    (Izmir Institute of Technology, 2016-07) Kıbrıs, Erman; Artok, Levent
    1,3-Substitution reactions of allylic compounds having a good leaving group is a prominent method in Organic Chemistry for the synthesis of new allylic reagents with an exchanged functional group. These reactions usually require the use of metal catalysts and one of the most challenging aspects for these applications is the regio- and stereo-selectivity of the process for a wide range of substrate types. Other compounds such as vinyl epoxides are also acceptable for substitution reactions. An important advantage of using these reagents is that opening of the oxirane ring during the substitution process lead to the generation of a hydroxyl group and as a result affords allyl alcohols which are important intermediaries in organic syntheses. An example of regio-selective metal-catalyzed reactions of vinyl epoxides having a terminal alkenyl group with environmentally benign organoborons was reported in the literature. However, no such success could be achieved with vinyl epoxides with an internal alkenyl group. Therefore, within the context of this method internal vinyl epoxides were successfully subjected to 1,3-substitution reactions with organoborons which yielded arylated allyl alcohols in both a regio- and stereo-selective manner. The method is applicable under quite mild conditions where a palladium-AsPh3 combination is used to activate the process.