Catalytic C−O Bond Cleavage of 2-Aryloxy-1-arylethanols and Its Application to the Depolymerization of Lignin-Related Polymers

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• 作者：Jason M. Nichols ; Lee M. Bishop ; Robert G. Bergman ; Jonathan A. Ellman
• 刊名：Journal of the American Chemical Society
• 出版年：2010
• 出版时间：September 15, 2010
• 年：2010
• 卷：132
• 期：36
• 页码：12554-12555
• 全文大小：162K
• 年卷期：v.132,no.36(September 15, 2010)
• ISSN：1520-5126

文摘

A ruthenium-catalyzed, redox neutral C−O bond cleavage of 2-aryloxy-1-arylethanols was developed that yields cleavage products in 62−98% isolated yield. This reaction is applicable to breaking the key ethereal bond found in lignin-related polymers. The bond transformation proceeds by a tandem dehydrogenation/reductive ether cleavage. Initial mechanistic investigations indicate that the ether cleavage is most likely an organometallic C−O activation. A catalytic depolymerization of a lignin-related polymer quantitatively yields the corresponding monomer with no added reagent.