Catalytic constructive deoxygenation of lignin-derived phenols: new C-C bond formation processes from imidazole-sulfonates and ether cleavage reactions.

Stuart M Leckie,Matthew L Clarke,Gavin J Harkness

doi:10.1039/c4cc04939j

Stuart M Leckie, Matthew L Clarke + Show 1 more

Open Access

https://doi.org/10.1039/c4cc04939j

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Abstract

As part of a programme aimed at exploiting lignin as a chemical feedstock for less oxygenated fine chemicals, several catalytic C-C bond forming reactions utilising guaiacol imidazole sulfonate are demonstrated. These include the cross-coupling of a Grignard, a non-toxic cyanide source, a benzoxazole, and nitromethane. A modified Meyers reaction is used to accomplish a second constructive deoxygenation on a benzoxazole functionalised anisole.

Highlights

As part of a programme aimed at exploiting lignin as a chemical feedstock for less oxygenated fine chemicals, several catalytic C–C bond forming reactions utilising guaiacol imidazole sulfonate are demonstrated
The production of cellulose-derived chemicals is significantly more commercially attractive if economic value can be obtained from the lignin fraction of ligno-cellulose
We considered a new challenge in this field of renewable chemistry; if a small portion of lignin-derived bio-oils can be converted into one or more higher value fine chemicals, prior to hydro-deoxygenation, extra economic value can be derived from this lignin fraction

Summary

Introduction

As part of a programme aimed at exploiting lignin as a chemical feedstock for less oxygenated fine chemicals, several catalytic C–C bond forming reactions utilising guaiacol imidazole sulfonate are demonstrated. Scheme 1 Catalytic constructive deoxygenation of 2-methoxyphenol might allow this lignin-derived feedstock to be used to produce less oxygenated aromatic compounds (R1/R2 = various alkyl/aryl groups).

Results

Conclusion