Abstract
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 (β-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 biomassrelated degradation to useful products.
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