Safe and practical ex-situ chlorination of electronically diverse π-systems

Direct chlorination of organic molecules is a powerful tool in organic synthesis. However, the employment of Cl₂ gas has some significant safety and logistical drawbacks. Recently, in-situ chlorination procedures have been developed to circumvent these limitations; however, these approaches require the use of harsh or expensive reagents and are limited in substrate scope. Herein we describe a safe and practical setup for ex-situ chlorine generation using a two-chamber COware system. Using this strategy, chlorination of electron-deficient, -neutral, and -rich π-systems can be achieved with good efficiency. Overall, this approach serves as a broadly applicable alternative to currently reported protocols and is suitable for laboratories in the academic setting.