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Issue 4, 2013

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

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Abstract

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.

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

Supplementary files

Article information


Submitted
17 Dec 2012
Accepted
17 Jan 2013
First published
07 Feb 2013

Chem. Sci., 2013,4, 1640-1645
Article type
Edge Article

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

A. Fedorov, A. A. Toutov, N. A. Swisher and R. H. Grubbs, Chem. Sci., 2013, 4, 1640 DOI: 10.1039/C3SC22256J

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