Fig. 5: Generation of 5-substituted hexahydro-1H-1,4-methanocarbazoles with various electrophiles.

Reaction conditions: [a]2-iodo-N-methylaniline (1.0 eq.), NBE-5,6-diCOOiPr (1.0 eq.), N-benzoyloxyamine (1.3 eq.), Pd(OAc)2 (5% eq.), TFP (10% eq.), Cs2CO3 (2.5 eq.), toluene, 100 oC, 12 h; [b]arylbromide (1.3 eq.), and DMF were used instead; [c]n-pentylbromide (1.3 eq.), PPh3 (10% eq.), and DMF were used instead; [d] benzoic anhydride (1.3 eq.), PdCl2 (5% eq.), and DME were used instead.