Halodealkenylation:\nOzonolysis and Catalytic Fe<sup>II</sup> with Vitamin C Convert C(sp<sup>3</sup>)–C(sp<sup>2</sup>) Bonds to C(sp<sup>3</sup>)–Halide\nBonds
BradyW. Dehnert (20404345)Youwei Yin (20404348)Ohyun Kwon (200984)
Abstract
As part of our investigations into\nC–C bond scission\nand\nfunctionalization, we report a halodealkenylation in which the C(sp<sup>3</sup>)–C(sp<sup>2</sup>) bonds of alkenes are cleaved and\nC(sp<sup>3</sup>)–halide bonds are formed, via a radical intermediate.\nThese transformations occur through Criegee ozonolysis and Fe<sup>II</sup>-catalyzed reductive coupling assisted by vitamin C as a\nstoichiometric reductant. We applied this strategy to the formal synthesis\nof (<i>R,R,R</i>)-γ-tocopherol.
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