Deaminative coupling of benzylamines and arylboronic acids

A metal-free deaminative coupling of non-prefunctionalised benzylamines and arylboronic acids is reported. In this operationally simple reaction, a primary amine in benzylamine is converted into a good leaving group in situ using inexpensive and commercially available isoamyl nitrite as a nitrosating reagent. Lewis-acidic arylboronic acids are shown to replace mineral acids such as HCl or HBF(4) that are conventionally used in the preparation of aryl diazonium salts. This unlocked the formation of the corresponding diarylmethanes by forging a new C–C bond in good yields.