Vinylation of Aryl Ether (Lignin β‐O‐4 Linkage) and Epoxides with Calcium Carbide through C−O Bond Cleavage. Issue 16 (4th August 2017)

• Record Type: Journal Article
• Authors: Teong, Siew Ping; Lim, Jenny; Zhang, Yugen
• Is Part Of: ChemSusChem. Volume 10:Issue 16(2017)
• Page Start: 3198
• Page End: 3201
• Publication Date: 2017-08-04
• Subjects: aryl ether -- bond cleavage -- calcium carbide -- epoxide vinylation -- lignin depolymerization; Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.201701153
• Languages: English
• ISSNs: 1864-5631

Abstract

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. Abstract : Valued vinyl : A mild and transition‐metal‐free protocol for the vinylation of epoxides and aryl‐ether linkage (β‐O‐4 lignin model compound) with calcium carbide through C−O bond cleavage is proposed, forming valuable vinyl ether products.