Table 4.

Synthesis of 2-allyl pyrrolidines and indolines via tandem reactions of primary amines.^[a]

Entry	Amine	Aryl bromide	Vinyl bromide	Product (E/Z ratio)[b]	Yield [%][b]
1					65[c],[e],[f]
2					50[c],[e],[f] (>20:1 dr)
3					60[d],[f]
4					69[d]

^[a]Conditions: amine (1.0 equiv), aryl bromide (1.0 equiv), NaOt-Bu (2.4 equiv), Pd₂(dba)₃ (1 mol%), 2-di-t-butylphosphinobiphenyl(2 mol%), toluene (0.25 M), 60–80 °C, then dppe or DPEphos (2 mol%) and vinyl bromide (1.2 equiv), 105–110 °C.

^[b]Product ratios refer to the isolated material, as judged by ¹H NMR analysis. Product ratios and yields refer to the average of two or more experiments.

^[c]This reaction was conducted with dppe as the second ligand.

^[d]This reaction was conducted with DPEphos as the second ligand.

^[e]This material contained ~3–10 % of an inseparable regioisomer analogous to 4a.

^[f]This material contained ~7–10 % of an inseparable impurity analogous to 5a.