Journal
CHEMSUSCHEM
Volume 10, Issue 16, Pages 3198-3201Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201701153
Keywords
aryl ether; bond cleavage; calcium carbide; epoxide vinylation; lignin depolymerization
Funding
- Institute of Bioengineering and Nanotechnology (Biomedical Research Council, Agency for Science, Technology and Research, Singapore)
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Calcium carbide has been increasingly used as a sustainable, easy-to-handle, and low-cost feedstock in organic synthesis. Currently, methodologies of using calcium carbide as solid acetylene in synthesis are strictly limited to activation and reaction with X-H (X = C, N, O, S) bonds. Herein, a mild and transition-metal-free protocol was developed for the vinylation of epoxides and aryl ether linkage (beta-O-4 lignin model compound) with calcium carbide through C-O bond cleavage, forming valuable vinyl ether products. Calcium carbide plays a vital role in the C-O bond activation and cleavage, and in providing acetylide source for the formation of vinylated products. These exciting results may provide new methodologies for organic synthesis and new insights toward lignin-or biomass-related degradation to useful products.
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