Orthogonal Nanoparticle Catalysis with Organogermaniums.

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ID: 54412
2019
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Abstract
Although nanoparticles are widely used as catalysts, little is known about their potential ability to trigger privileged transfor-mations as compared to homogeneous molecular or bulk heterogeneous catalysts. We herein demonstrate (and rationalize) that nanoparticles display orthogonal reactivity to molecular catalysts in the cross-coupling of aryl halides with aryl germanes. While the aryl germanes are unreactive in LnPd(0)/LnPd(II) catalysis and allow selective functionalization of established coupling partners in their presence, they display superior reactivity under Pd nanoparticle conditions, outcompeting established coupling partners (such as e.g. ArBPin, ArBMIDA ) and allowing air-tolerant, base-free and orthogonal access to valuable and challenging biaryl motifs. As opposed to the notoriously unstable polyfluoroaryl and 2-pyridyl boronic acids, the corresponding germanes are highly stable and readily coupled. Our mechanistic and computational studies provide unambiguous support of nanoparticle catalysis and suggest that owing to the electron-richness of aryl germanes, they preferentially react via electrophilic-aromatic substitution, and in turn are preferentially activated by the more electrophilic nanoparticles.
Reference Key
fricke2019orthogonalangewandte Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Fricke, Christoph;Sherborne, Grant;Funes-Ardoiz, Ignacio;Senol, Erdem;Guven, Sinem;Schoenebeck, Franziska;
Journal angewandte chemie (international ed in english)
Year 2019
DOI
10.1002/anie.201910060
URL
Keywords
chemoselectivity, catalysis, cross-coupling, dft, synthesis

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