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Published February 7, 2013 | Supplemental Material
Journal Article Open

Lewis-base silane activation: from reductive cleavage of aryl ethers to selective ortho-silylation


We report a transition-metal-free protocol for the efficient reductive cleavage of diaryl and aryl alkyl ethers. The combination of triethylsilane with common bases forms an unusually powerful reductive couple that regioselectively ruptures lignin- and coal-related C–O bonds in aromatic ethers. Interestingly, with certain bases and temperature regimes ortho-directed C–H silylation efficiently competes with the latter process. However, careful tuning of the reactions conditions allows for the selective reductive cleavage of lignin model compounds to their corresponding phenolic and aromatic constituents.

Additional Information

© 2013 Royal Society of Chemistry. Received 17th December 2012; Accepted 17th January 2013. First published on the web 07 Feb 2013. Support of this work from BP under the XC2 program is gratefully acknowledged. A.A.T. is grateful to NSERC for a PGS D fellowship. A. F. thanks Dr Erik P. A. Couzijn (ETH Zürich) for helpful discussions.

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