Heck reaction thesis

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Development of the first and second-generation Silyl-Heck reactions

The Heck reaction is a famous chemical reaction discovered by Mizoroki and Heck in through independent research. It involves the cross-coupling reaction between organohalides and alkenes, these two substances react in the presence of a palladium catalyst and a base to form a substituted alkene:. Step A is the oxidative addition of a polar substrate onto a palladium catalyst to form a tetrasubstituted complex. Step B is the migratory insertion of an olefin into the system. It is noteworthy that the first step of the catalytic cycle is actually not the oxidative addition of the substrate, as the palladium catalyst must be activated before the reaction. Therefore, a thorough study of the structure of the palladium catalyst and its properties will be important in understanding Heck reactions [2]. The catalytic precursor Pd II OAc 2 , associated with monodentate phosphine ligands such as PPh 3 is normally used to catalyze the reaction, but this Pd II complex must be reduced to Pd 0 in order to enter the catalytic cycle.
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Larry E. Overman

Abstract: Allyl and vinylsilanes are important nucleophiles in organic synthesis. They are stable reagents that can participate in a variety of transformations including mainly Hosomi-Sakurai crotylations, Hiyama-Denmark crosscouplings, Tamao-Fleming oxidations, and fluorination reactions. Prior to this work there were few methods that allowed for the synthesis of these valuable compounds from simple alkenes. Using transition metal catalysis, I sought to develop a method to access unsaturated organosilanes using a reaction analogous to the Heck reaction. The latter reaction is highly selective for the linear E-allylsilane.
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Related Reactions Stille Coupling Olefinations. The palladium-catalyzed C-C coupling between aryl halides or vinyl halides and activated alkenes in the presence of a base is referred as the "Heck Reaction". Recent developments in the catalysts and reaction conditions have resulted in a much broader range of donors and acceptors being amenable to the Heck Reaction. Kantam, P.
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