The Fe(iii)-catalyzed decarboxylative cycloaddition of β-ketoacids and 2H-azirines for the synthesis of pyrrole derivatives. Issue 22 (20th October 2020)

• Record Type: Journal Article
• Authors: Hu, Haipeng; Wang, Cuilin; Lai, Han; Wang, Siyuan; Ni, Hailiang; Yu, Wenhao; Cao, Peng
• Is Part Of: Organic chemistry frontiers. Volume 7:Issue 22(2020)
• Page Start: 3686
• Page End: 3691
• Publication Date: 2020-10-20
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d0qo00951b
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : An Fe(iii )-catalyzed Mannich/decarboxylative ring expansion reaction to generate pyrrole derivatives has been achieved using Fe(OTf)3 as the catalyst. A series of pyrrole derivatives was obtained in moderate to excellent yields. Abstract : An Fe(iii )-catalyzed Mannich/decarboxylative ring-expansion reaction for the synthesis of pyrrole derivatives is reported. β-Ketoacids were employed as enolate equivalents of a simple ketone and were coupled with 2 H -azirine in a formal [3 + 2] cycloaddition reaction. A series of di-, tri-alkyl/aryl-substituted and fused pyrrole derivatives was obtained in moderate to excellent yields (17–92%) under mild reaction conditions. The products could be synthesized on gram-scale with 5 mol% catalyst loading.