A simple and atom-economical protocol for bis-nitration of 1naphthylamides was firstly discovered with tert-butyl nitrite (TBN) as nitro source and catalyzed by Cu(OAc) 2 . Assisted by picolinamide direction, the C2,4-H bis-nitration could be achieved with excess amount of TBN at 50°C in HOAc. A radical pathway and single electron transfer process might be involved in the bis-nitration process.[a] Prof. Scheme 1. Regioselective CÀ H mono-and bis-nitration of quinoline and naphthalene amides via SET mechanism.
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