Reported herein is a transition-metal-free protocol for the efficient reductive cleavage of diaryl and aryl alkyl ethers. The combination of triethylsilane with simple bases forms an unusually powerful reductive couple that affords regioselective rupture of lignin- and coal-related C-O bonds in aromatic ethers. Interestingly, this is accompanied by ortho-directed C-H silylation that be-comes preferred with certain bases and temperature re-gimes. However, the tuning of selectivity proved possible thus enabling the development of a practical method for the title transformation, as illustrated by the reduction of lignin model compounds to their corresponding phenolic and aromatic constituents.

Transition-metal-free reductive cleavage of lignin-related C-O bonds by an activated silane

245th National Meeting (2013)

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