N-aryl tetrahydroisoquinolines

Li and Li have reported Cu(I)-catalyzed enantioselective alkynylation of prochiral sp C-H bonds adjacent to a nitrogen atom [58]. In this approach, a combination of CuOTf and pybox (197) in the presence of t-BuOOH results in coupling of N-aryl tetrahydroisoquinolines (209) with terminal alkynes (Scheme 17.42). The desired coupling products (211) were generally isolated in moderate to good yields with moderate enantioselectivities. Although it is not clear if the catalytically active Cu(I) species acts as a Lewis acid in this protocol, the chemistry is, nonetheless, worthy of mention. 

N-aryl-tetrahydroisoquinolines were the subject of a gold-catalyzed oxidative coupling with diarylphosphine oxides to provide the corresponding phosphinoyl derivatives (Scheme 26). ... 

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