The aryl phosphonate moiety is found in many bioactive compounds such as pharmaceuticals and agrochemicals. Traditionally, these compounds are synthesized from highly reactive Grignard reagents. In the past decade, transition-metal catalysts have enabled the synthesis of these aryl phosphonates under milder reaction conditions. However, due to the intrinsic toxicity and high cost of rare metals, the development of alterative synthetic routes has been gaining traction. Recently, photoredox catalysis has been successfully used for the synthesis of aryl phosphonate, but these methods often require metal-based photocatalysts. Herein, we report the photo-induced synthesis of aryl phosphonates from aryl iodides under metal-free and photocatalyst-free conditions. This methodology proceeds at room temperature under very mild conditions using only DIPEA. The transformation of aryl iodide to aryl phosphonate proceeds in moderate to excellent yields and tolerates a wide range of functional groups and electronic parameters around the aromatic ring.

Light-mediated phosphonation of aryl iodides using DIPEA and trialkyl phosphites

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