Photochemical Oximesulfonylation of Alkenes Using Sulfonyl-Oxime-Ethers as Bifunctional Reagents

Utilization of oxime ethers as bifunctional reagents remains unknown. Herein, we present a mechanistically distinct strategy that enables oximesulfonylation of olefins using sulfonyl-oxime-ethers as bifunctional reagents under metal-free photochemical conditions. Via concomitant C-S and C-C bond formation, the process permits incorporation of oxime and sulfonyl groups into olefins in a complete atom-economic fashion, providing rapid access to multi-functionalized & beta;-sulfonyl oxime ethers with good yields and stereoselectivity. The method is amenable to functionalization of complex bioactive molecules and is shown to be scalable. A radical chain mechanism initiated via photochemical Hydrogen Atom Transfer (HAT) mediated N-O bond cleavage is suggested for the process, based on our results on mechanistic investigations. An efficient metal free photochemical method for regioselective incorporation of oxime ether and sulfonyl functionality to olefin using sulfonyl-oxime-ethers as bifunctional reagents is demonstrated. The process exhibits a wide range of substrate scope providing rapid access to 1,2-oximesulfonylated products in good to excellent yields and diastereoselectivity.image