Oximes are pharmacophores and precursors to a large number of important functional groups. While many useful strategies for the synthesis of oximes are reported, they require functionalized substrates like olefins, carbonyl compounds, alkyl halides, alcohols, alkyl carboxylic acids, etc. On the contrary, the synthesis of functionalized oximes via direct incorporation of oxime functional group at inert C(sp3)-H bond has emerged as the most appealing strategy to such targets but remains relatively unexplored. Hence, there is an urgent need to develop a new generation synthetic protocol for the synthesis of functionalized oximes via the direct introduction of oxime functional group at C(sp3)-H bonds under mild conditions avoiding the use of toxic reagents/additives. In this context, we have recently developed a light-induced aerobic method for the synthesis of functionalized oximes via direct coupling of several chemical feedstocks with sulfone-containing oxime using inexpensive hydrogen atom transfer (HAT)-organophotocatalyst and air as the sole oxidant. This light-induced HAT catalysis enables the synthesis of various functionalized oxime molecules in good yields using a relatively low substrate/sulfone ratio under benign conditions. The design, development, substrate scope, and mechanistic investigations of the reaction will be discussed in detail during the presentation.

Direct introduction of oxime functional group at C(sp3)-H bond via aerobic light-induced HAT-organophotocatalysis

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