Science of Synthesis

Gnanaprakasam, B.; Chaudhari, M. B., Science of Synthesis Knowledge Updates, (2019) 2, 407.

In previous decades, alkyl and aryl hydroperoxides have been extensively used both as radical initiators and also as terminal oxidants in a variety of reactions. Because of their commercial availability and excellent reactivity, alkyl hydroperoxides have also been applied in the peroxidation of functionalized or non-functionalized hydrocarbons. Recently, there has been an upsurge in reports on the metal-catalyzed peroxidation of various organic compounds, and these are discussed in the following sections. Peroxides are inexpensive and common radical initiators; typical examples include tert-butyl hydroperoxide, dibenzoyl peroxide (DBPO), and cumene hydroperoxide (CHP).[‌1‌] Use of oxophilic metal catalysts is advantageous for the activation of alkyl hydroperoxides. The alkyl hydroperoxides react vigorously with metals to afford an alkoxy radical and a hydroxide ion (‌Scheme 1‌); as a consequence, the metal facilitates the radical–radical cross-coupling reaction with a variety of partners.[‌2‌]

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