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  • Title: Catalytic functionalization of unactivated sp3 C-H bonds via exo-directing groups: synthesis of chemically differentiated 1,2-diols.
    Author: Ren Z, Mo F, Dong G.
    Journal: J Am Chem Soc; 2012 Oct 17; 134(41):16991-4. PubMed ID: 23030547.
    Abstract:
    We describe a Pd-catalyzed site-selective functionalization of unactivated aliphatic C-H bonds, providing chemically differentiated 1,2-diols from monoalcohol derivatives. The oxime was employed as both a directing group (DG) and an alcohol surrogate for this transformation. As demonstrated in a range of substrates, the C-H bonds β to the oxime group are selectively oxidized. Besides activation of the methyl groups, methylene groups (CH(2)) in cyclic substrates and methine groups (CH) at bridge-head positions can also be functionalized. In addition, an intriguing oxidative skeleton rearrangement was observed using the menthol-derived substrate. The use of exo-directing groups in C-H activation, as illustrated in this work, would potentially open doors for the discovery of new transformations and new cleavable DGs.
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