The inherent reactivity of lignin in conventional biomass processing commonly prevents isolation of native lignin and limits monomer yields from catalytic depolymerization strategies that target aryl-ether bonds. Here we show...
An auto-tandem catalytic double allylic
rearrangement of N-alloc-N-allyl
ynamides was developed.
This reaction proceeds through two separate and distinct catalytic
cycles with both decarboxylative Pd−π-allyl and Pd(0)-promoted
aza-Claisen rearrangements occurring. A detailed mechanistic study
supported by computations highlights these two separate mechanisms.
Previously unreported reversible C–N ionization and a Pd(0)-catalyzed
[3,3]-sigmatropic rearrangement were discovered. This study provides
new reaction pathways for both π-allyl and sigmatropic rearrangements.
Lignin valorization approaches, which are critical to biorefining, often involve depolymerization to aromatic monomers. Alkaline oxidation has long held promise as a lignin depolymerization strategy, but requires high concentrations of...
Correction for ‘Flow-through solvolysis enables production of native-like lignin from biomass’ by David G. Brandner et al., Green Chem., 2021, 23, 5437–5441, DOI: 10.1039/D1GC01591E.
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