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38.10.4.12 Peroxidation of Methylanilines Using Ruthenium

DOI: 10.1055/sos-SD-138-00001

Gnanaprakasam, B.; Chaudhari, M. B.Science of Synthesis Knowledge Updates, (20192439.

For previous information on ruthenium-catalyzed peroxidation of amines using tert-butyl hydroperoxide, see Section 38.5.1.6. The reaction of N,N-dimethylaniline with tert-butyl hydroperoxide in the presence of ruthenium–porphyrin complex 69 provides the peroxy compound N-[(tert-butylperoxy)methyl]-N-methylaniline (70) (Scheme 39).[‌44‌] In the original report, the C3-alkylation of indoles via oxidative coupling of the tertiary amine is described, with compound 70 acting as an intermediate for this alkylation reaction.

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