3 years ago

Cooperative Polar/Steric Strategy in Achieving Site-Selective Photocatalyzed C(sp3)−H Functionalization

Cooperative Polar/Steric Strategy in Achieving Site-Selective Photocatalyzed C(sp3)−H Functionalization
Maurizio Fagnoni, Takahide Fukuyama, Ilhyong Ryu, Davide Ravelli, Keiichi Yamada, Saki Fujii
Synergistic control over the SH2 transition states of hydrogen abstraction exploiting polar and steric effects provides a promising cooperative strategy for site-selective C(sp3)−H functionalization using decatungstate anion photocatalysis. By using this photocatalytic approach, the C−H bonds of substituted lactones and cyclic ketones were functionalized selectively. In the remarkable case of 2-isoamyl 4-tert-butyl cyclohexanone (1 t) bearing five methyl, five methylene, and three methine C−H bonds, one methine C−H bond in the isoamyl tether was selectively functionalized. Synergistic control over the SH2 transition states of hydrogen abstraction by polar and steric effects provides promising insight into site-selective C(sp3)−H functionalization using decatungstate anion ([W10O32]4−) photocatalyt. Even with many possible C−H reaction sites, transformation only occurs at the positions marked in blue for the given molecules.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701865

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