Optimization and Mechanistic Elucidation of Vinylgermanium Coupling to Iodobenzene
Tanemura, Kiyoto A.
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Carbon—Carbon coupling reactions play an important role in the synthesis of structurally complex organic molecules that are of interest to the materials, pharmaceutical, and agricultural industries. A new vinylgermanium coupling reaction that inverts the alkene geometry from E to Z might offer a wider control over olefin geometry in synthesis. The Pd-catalyzed coupling of E-2-methyl-4- (tributylgermyl)but-3-en-2-ol to iodobenzene under Heck-type conditions produced the Z-product as the major product. To optimize the conversion and the selectivity for the Z-product and gain a deeper understanding of the reaction mechanism, reaction conditions were explored. Previous mechanistic explanation were reconsidered, as dissolved dioxygen played a role in the reaction mechanism.