Recently we have reported the use of platinum to mediate the non-directed C-H functionalization of aliphatic amines. This poster describes the mechanistic studies that have been conducted to further understand both the regioselectivity and chemoselectivity of the Pt-catalyzed, terminal-selective C-H functionalization. Our findings suggest that alkyl chain length and chain branching have a significant impact on both the reactivity and observed regioselectivity of C-H functionalization. H/D exchange experiments corroborate well with these observed selectivities. In addition, time-study experiments and synthesis of authentic intermediates provide evidence for the initial formation of terminal C-H chlorination products followed by hydrolysis to form the C-H hydroxylation products. Under our optimized conditions, CuCl2 serves as the stoichiometric oxidant; however, there is evidence for the re-oxidation of Cu(I) to Cu(II) with dioxygen.

Mechanistic insights into non-directed, platinum-catalyzed C(sp3)-H functionalization

251st National Meeting (2016)

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