Addition of aryl isocyanides to various ruthenium-based metathesis catalysts causes a net carbene insertion/ring expansion (Buchner reaction) into one of the aromatic rings of the N-heterocyclic carbene ligand. In our mechanistic studies, this very fast reaction is used to quench metathesis activity. In a practical application, isocyanides can be used to efficiently remove ruthenium from the organic product. To be used as a quenching reaction, fast kinetics are required. In this study the rate of Buchner reaction was studied by low temperature <i>in situ</i> IR measurements. The effect of the isocyanide, the N-aryl substituent and the structure of the carbene group were each studied in the rate of insertion. Results with additional Grubbs catalysts will also be presented.

Mechanistic studies of isocyanide promoted Buchner insertion reactions with Ruthenium-based metathesis catalysts

249th National Meeting (2015)

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