Cu catalyzed [4 + 2] cycloaddition for the synthesis of highly substituted 3-fluoropyridines. Issue 18 (25th April 2022)

• Record Type: Journal Article
• Authors: Fu, Yiwei; Shi, Haoyu; Lei, Shengshu; Shi, Lei; Li, Hao
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 18(2022)
• Page Start: 3731
• Page End: 3736
• Publication Date: 2022-04-25
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00133k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A copper catalyzed [4 + 2]annulation–aromatization of benzyl trifluoromethyl ketimines with 3-acryloyloxazolidin-2-ones has been developed for the synthesis of 3-fluoropyridines in moderate yields through double C–F bond cleavages. Abstract : A copper catalyzed annulation–aromatization of benzyl trifluoromethyl ketimines with 3-acryloyloxazolidin-2-ones for the synthesis of 3-fluoropyridines through double C–F bond cleavages has been developed. In this approach, the annulation occurred between the in situ formed dienes from trifluoromethyl ketimines via the first C-F bond cleavage and 3-acryloyloxazolidin-2-ones. Then the aromatization afforded 3-fluoropyridines in moderate yields through the second C–F bond cleavage. The 3-fluoropyridine products could be further hydrolyzed to multi-substituted 3-pyridinecarboxylic acids.