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Germylation of Arenes via Pd(I) Dimer Enabled Sulfonium Salt Functionalization

Aymane Selmani, Avetik G. Gevondian, Franziska Schoenebeck

2020Organic Letters73 citationsDOI

Abstract

While aryl germanes have recently found usage as coupling partners in powerful catalytic applications, the synthetic access to this promising functionality is currently limited. This report details the straightforward synthesis of functionalized aryl triethylgermanes via formal C–H functionalization. Building on the concept of directing-group-free and site-selective C–H functionalization of arenes to thianthrenium salt intermediates, we showcase their efficient couplings with triethylgermane (Et3Ge–H) at room temperature, which was enabled by the air- and moisture-stable Pd(I) dimer, [Pd(μ-I)(PtBu3)]2. The method tolerates numerous functional groups, including valuable (pseudo)halides.

Topics & Concepts

SulfoniumSurface modificationChemistryArylSalt (chemistry)Combinatorial chemistryHalideDimerCatalysisOrganic chemistryPhysical chemistryAlkylCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSulfur-Based Synthesis Techniques
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