Unique Regioselectivity in the C(sp<sup>3</sup>)–H α‑Alkylation of Amines: The Benzoxazole Moiety as a Removable Directing Group

2014-08-15T00:00:00Z (GMT) by Günther Lahm Till Opatz
The benzoxazol-2-yl- substituent was found to act as a removable activating and directing group in the Ir-catalyzed alkylation of C­(sp<sup>3</sup>)–H bonds adjacent to nitrogen in secondary amines. It can be easily introduced by oxidative coupling or by an S<sub>N</sub>Ar reaction, and it can be removed by hydroxide or by hydride reduction. For 1,2,3,4-tetra­hydroiso­quinolines, activation exclusively takes place in the 3-position. A variety of activated as well as unactivated terminal olefins are suitable reaction partners.