Transformative Masked Ortho‐Quinone Chemistry: From Direct Guaiacol Activation to Lignin‐Based Adhesives

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Abstract
Guaiacol moieties (1‐hydroxy‐2‐methoxy‐benzenes) are among the most abundant structural motifs in renewable biophenolic feedstocks, representing a potential industrial‐scale stream from softwood lignin through biorefinery valorization. Here, the transformative chemistry of masked ortho‐quinones (MoQs) is introduced, yielding reactive guaiacol derivatives to enable thiol‐guaiacol connectivity (TGC) polymers. Phenyliodine(III)diacetate (PIDA) oxidizes guaiacols to chemically pure MoQs within minutes at room temperature, generating activated triguaiacol monomers that undergo thiol‐MoQ Michael‐type polyaddition with multithiols. This bulk polymerization leads to TGC‐adhesives, reaching professional performance lap‐shear strengths up to 16.9 ± 0.9 MPa. The robust strategy is extended to directly activate technical lignin, generating curable multi‐MoQ prepolymers which bond aluminum with lap‐shear strengths of 9.1 ± 0.7 MPa, positioning MoQs as a sustainable platform chemistry to bridge from lignin to high‐performance materials.

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