Deoxygenation of oximes for the synthesis of pyrrolines via hydroimination cyclization. Issue 16 (5th April 2023)

• Record Type: Journal Article
• Authors: Han, Wencheng; Liu, Wen-Deng; Su, Junqi; Zhao, Jiannan
• Is Part Of: Organic & biomolecular chemistry. Volume 21:Issue 16(2023)
• Page Start: 3350
• Page End: 3354
• Publication Date: 2023-04-05
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d3ob00072a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A series of pyrrolines were synthesized via cyclization of iminyl radicals, which were generated by photocatalytic deoxygenation of oximes with trivalent phosphine. Abstract : Herein, we report the generation of iminyl radicals through photocatalytic deoxygenation of oximes with trivalent phosphine. The hydroimination reaction proceeded via β-scission of a phosphoranyl radical, followed by 5- exo-trig cyclization of the resulting iminyl radical. This protocol transforms oximes, including alkyl oximes, into a variety of pyrrolines in moderate to good yields. A radical clock experiment confirmed the formation of a cyclic radical and supported our reaction design.