Figure 1.

Various ways of generating complexity from simple precursors. (A) Application of photocycloaddition to prepare syn- and anti-spiroindane pyrrolidines. (B) Nickel-catalyzed method complementary to panel (A) of synthesizing indanyl amines through the reductive coupling of ortho-haloaryl pyrrolines and olefins. (C) Nickel was superior to palladium, which forms too stable a complex upon oxidative addition (1, CCDC 2082427) (D). Treating o-bromophenylpyrroline, o-BPP, with stoichiometric nickel at elevated temperature leads to the formation of syn adduct 2, the homocoupled biaryl 3, and reduced 2-phenylpyrroline.