Benzylic Hydroxylation

Direct C-H oxidation is very difficult but extremely important, as it occurs in some important biological processes.20 The presence of some kind of activating group such as an aryl or alkenyl group offers some encouragement for success. Benzylic hydroxylation can be effected using iodosylbenzene and an iron oxo species derived from a porphyrin (Figure 11.10).21 Such reactions mirror the role of cytochrome P-450 in monooxygenase enzyme processes. The yields obtained for benzylic hydroxylation are only moderate, as is the enantioselectivity.

Catalyst M = FeCI

Catalyst M = FeCI

PhIO

Fe porphyrin complex catalyst

Strap

Strap

Figure 11.10 Enantioselective benzylic hydroxylation.

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  • manuela freytag
    What is benzylic hydroxylation?
    8 years ago

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