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Vinylation of Aryl Ether (Lignin β‐O‐4 Linkage) and Epoxides with Calcium Carbide through C−O Bond Cleavage
Author(s) -
Teong Siew Ping,
Lim Jenny,
Zhang Yugen
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201701153
Subject(s) - ether , bond cleavage , calcium carbide , chemistry , aryl , acetylene , lignin , organic chemistry , ether cleavage , carbide , calcium , polymer chemistry , catalysis , alkyl
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.