Iodine-catalysed transfer hydrogenation of a carbon–carbon σ-bond with water†
Ching Tat
To 
‡a
and
Kin Shing
Chan
*a
‡a
and
Kin Shing
Chan
*a
Abstract
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.
- This article is part of the themed collection: Synthetic methodology in OBC
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