Lignin is a recalcitrant and underexplored natural feedstock for aromatic commodity chemicals. Improving current lignin fragmentation technologies, which generally suffer from harsh conditions along with low yields and selectivity of the obtained products, would represent an important advance towards a more sustainable future. Herein we describe a high yielding one-pot methodology for cleavage of lignin C–O bonds under mild conditions at ambient temperature. The replacement of a chemical oxidant with an <i>N</i>-hydroxyphthalimide (NHPI)/2,6-lutidine catalyst system in an electrochemical cell proved to smoothly deliver selective benzylic oxidation of lignin dimers as well as act as an innocent spectator during the photocatalytic C–O bond cleavage, offering an ideal combination to affect the overall transformation in a single reaction vessel. The operational simplicity and excellent mass recovery of the process provides a unique opportunity to expand the existing lignin usage from energy to commodity chemicals source.

One-pot electrocatalytic oxidation/photocatalytic C–O bond cleavage of lignin systems at ambient temperature

253rd National Meeting (2017)

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