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Organogermanes as Orthogonal Coupling Partners in Synthesis and Catalysis

Christoph Fricke, Franziska Schoenebeck

2020Accounts of Chemical Research146 citationsDOI

Abstract

catalysis all of the other established groups can be functionalized preferentially over the Ge functionality. We similarly were able to harness this orthogonal reactivity mode in oxidative gold catalysis, where organogermanes proved to be more reactive than the established silanes or boronic esters. We have also developed an orthogonal approach for metal-free halogenation of organogermanes with convenient halogenation agents, offering access to the chemo- and regioselective installation of valuable halide motifs in the presence of alternative groups that can also engage in electrophilic halogenations.In this Account, we wish to provide an overview of (i) the historic versus current reactivity findings and synthetic utility of organogermanes, (ii) the current state of mechanistic understanding of their reactivity, and (iii) the synthetic repertoire and ease of installing the germanium functionality in organic molecules.

Topics & Concepts

ArylTransmetalationContext (archaeology)Reactivity (psychology)SilanesChemistryElectrophileReagentCombinatorial chemistryOrganic synthesisCoupling reactionCatalysisOrganic chemistryAlkylBiologyPaleontologyPathologyAlternative medicineSilaneMedicineCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistryCatalytic C–H Functionalization Methods
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