Cyclopropanation of Alkenes with Halodiazirines as Halocarbene Precursors in Continuous Flow

Chemistry. 2024 May 17;30(28):e202303969. doi: 10.1002/chem.202303969. Epub 2024 Apr 9.

Abstract

The cyclopropanation reaction of alkenes with photolytically-generated chlorocarbenes from chlorodiazirines is reported as an effective way to prepare substituted 3-chloro-3-aryl-cyclopropanes. This practical and efficient approach allows the synthesis of various 3-chloro-3-aryl-cyclopropanes (32 examples) in continuous flow in 5-minute residence time under light-emitting diode (LED) irradiation. The conditions using 380 nm LED irradiation were successfully extended to the synthesis of substituted 3-bromo-3-aryl-cyclopropanes (3 examples).

Keywords: continuous flow; cyclopropanes; diazirines; halodiazirines; photochemistry.