Cyclopropanation of Alkenes with Halodiazirines as Halocarbene Precursors in Continuous Flow

• Published in: Chemistry : a European journal Vol. 30; no. 28; pp. e202303969 - n/a
• Main Authors: To, Hoang‐Minh, Ollevier, Thierry
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 17-05-2024
• Subjects: Alkenes; Aromatic compounds; Continuous flow; Cyclopropane; cyclopropanes; diazirines; halodiazirines; Irradiation; Light emitting diodes; Organic compounds; photochemistry; Radiation; Substitutes; Synthesis; continuous flow; cyclopropanes; diazirines; photochemistry; halodiazirines
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.202303969

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).
The preparation of substituted 3‐chloro‐3‐aryl‐cyclopropanes through the reaction of alkenes with photolytically‐generated chlorocarbenes from chlorodiazirines is reported as an effective method. This approach facilitates the production of diverse 3‐chloro‐3‐aryl‐cyclopropanes (32 examples) in an continuous flow with a residence time of 5 minutes under the influence of light‐emitting diode (LED) irradiation. The use of 380 nm irradiation conditions was effectively extended to the synthesis of substituted 3‐bromo‐3‐aryl‐cyclopropanes (3 examples).