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

Toutov, Anton A. and Fedorov, Alexey and Swisher, Nicholas A. and Grubbs, Robert H. (2013) Transition-metal-free reductive cleavage of lignin-related C-O bonds by an activated silane. In: 245th ACS National Meeting & Exposition, Abstracts of Papers, 7-11 April 2013, New Orleans, LA.

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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 arom. ethers. Interestingly, this is accompanied by ortho-directed C-H silylation that becomes preferred with certain bases and temp. 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 redn. of lignin model compds. to their corresponding phenolic and arom. constituents.

Item Type:Conference or Workshop Item (Paper)
Related URLs:
URLURL TypeDescription website
Toutov, Anton A.0000-0002-6561-0462
Fedorov, Alexey0000-0001-9814-6726
Swisher, Nicholas A.0000-0002-5320-407X
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2013 American Chemical Society.
Record Number:CaltechAUTHORS:20130729-103843842
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:39626
Deposited By: Tony Diaz
Deposited On:29 Jul 2013 21:21
Last Modified:07 Jul 2020 20:12

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