Deoxygenation of oximes for the synthesis of pyrrolines via hydroimination cyclization

Herein, we report the generation of iminyl radicals through photocatalytic deoxygenation of oximes with trivalent phosphine. The hydroimination reaction proceeded via beta-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.

Automated summary

In this study, iminyl radicals were generated through photocatalytic deoxygenation of oximes with trivalent phosphine. The hydroimination reaction proceeded via beta-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.