Iodine catalysed the transfer hydrogenation of a benzylic C-C σ-bond in [2.2]paracyclophane with water to yield 4,4'-dimethylbibenzyl. The C-C σ-bond was first cleaved by homolytic substitution with iodine radicals to produce a 4,4'-diiodomethylbibenzyl intermediate. The benzylic C-I bonds in this intermediate were subsequently reduced by HI, generated in situ from the disproportionation of I2 with H2O, to achieve transfer hydrogenation and regenerate I2.
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