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Regioselectivity in the Heck (Mizoroki-Heck) Reaction

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Selectivity in the Synthesis of Cyclic Sulfonamides

Part of the book series: Springer Theses ((Springer Theses))

Abstract

The alkenylation, or arylation of olefinic compounds in the presence of catalytic amounts of Pd(0) to give substituted olefins is referred to as the Heck (Mizoroki-Heck) reaction [1, 2]. This is a powerful tool used for the construction of carbon-carbon bonds, that often might otherwise be difficult to assemble [3–8]. Complex molecular structures [9–12], including those bearing asymmetric stereogenic centres [13] can be rapidly prepared and in addition, the reaction conditions used for this process can tolerate a wide range of functional groups. The active palladium catalyst can be generated in situ from air-stable precatalysts (e.g. Pd(OAc)2), and reactions are usually carried out at elevated temperatures, in the presence of base (bulky amines or inorganic salts) and monodentate or bidentate phosphine ligands. One significant limitation of the reaction is that substrates cannot contain a β-hydrogen. However, recent reports suggest conditions that can circumvent this constraint, albeit for a limited range of substrates (Scheme 2.1) [14, 15].

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  1. HCI F 308, ETH Zürich, Zürich, Switzerland

    Kimberly Geoghegan

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  1. Kimberly Geoghegan
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Correspondence to Kimberly Geoghegan .

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Geoghegan, K. (2014). Regioselectivity in the Heck (Mizoroki-Heck) Reaction. In: Selectivity in the Synthesis of Cyclic Sulfonamides. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-10338-9_2

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