Journal
ACS CATALYSIS
Volume 9, Issue 3, Pages 2252-2260Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b04172
Keywords
aerobic oxidation; C-O bond cleavage; lignin; photoredox catalysis; sustainable chemistry
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Funding
- NSF [CHE-1565782]
- Camille and Henry Dreyfus Foundation
- University of Michigan
- Department of Energy [DE-SC0006628]
- Rackham Graduate School at the University of Michigan
- Swedish Research Council [637-2013-7314]
- Royal Swedish Academy of Agriculture and Forestry (Kungliga Skogs-och Lantbruksakademien)
- Raman Areces Foundation (Becas para Estudios Postdoctorales)
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Lignin, which is a highly cross-linked and irregular biopolymer, is nature's most abundant source of aromatic compounds and constitutes an attractive renewable resource for the production of aromatic commodity chemicals. Herein, we demonstrate a practical and operationally simple two-step degradation approach involving Pd-catalyzed aerobic oxidation and visible-light photoredox-catalyzed reductive fragmentation for the chemoselective cleavage of the beta-O-4 linkage-the predominant linkage in lignin for the generation of lower-molecular-weight aromatic building blocks. The developed strategy affords the beta-O-4 bond cleaved products with high chemoselectivity and in high yields, is amenable to continuous flow processing, operates at ambient temperature and pressure, and is moisture- and oxygen-tolerant.
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