Table 2.

Palladium-catalyzed synthesis of N-phenyl-2-allylpyrroldines.^[a]

Entry	Vinyl bromide	Product (E/Z ratio)[b]	3/4[b]	Yield [%][b]
1			14:1	81[c]
2			17:1	85
3			17:1	89
4			13:1	78[d]
5			>20:1	88
6			19:1	77
7			>20:1	77
8			>20:1	87
9			>20:1	88

^[a]Conditions: amine 1 (1.0 equiv), vinyl bromide 2 (1.1–2.0 equiv), NaO t-Bu (1.2 equiv), Pd₂(dba)₃ (1 mol%), P(2-furyl)₃ (4 mol %), toluene (0.25 M), 60–110 °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 material contained ~5 % of 5a as an inseparable impurity.

^[d]This material contained ~10 % of 5d as an inseparable impurity.