Table 2.

Cascade Intramolecular N-Arylation/Intermolecular Carboamination Reactions

entry	substrate	product	catalystb	drc	yield (%)d
1			A	>25:1 (20:1)	76
2	(±)-5a		A	8:1 (5:1)	78
3	(±)-5a		Be	>25:1 (5:1)	42
4	(+)-5a 92% ee		B	8:1 (7:1) 86% ee	58
5			B	14:1 (5:1)	60
6	(−)-5d 87% ee		A	>25:1 (10:1) 91% ee	75
7			C	15:1 (3:1)	45
8			A	25:1 (12:1)	68
9	(±)-5b		A	22:1 (8:1)	63
10	(±)-5b		Be	7:1 (3:1)	56
11	(+)-5b 88% ee		B	>25:1 (10:1) 92% ee	56
12			B	11:1 (12:1)	79
13	(±)-5e		B	10:1 (7:1)	47
14			A	15:1 (5:1)	35

^aConditions: Reactions were conducted on a 0.25 mmol scale using 1.0 equiv of substrate, 1.2 equiv of ArCl, 2.4 equiv of NaO^tBu, catalyst (4 mol % [Pd]), toluene (0.25 M), 100 °C.

^bCatalyst A: Pd(OAc)₂ (4 mol %), Cy₄Dpe-Phos 15 (4 mol %). Catalyst B: Pd₂(dba)₃ (2 mol % complex), PCy₃•HBF₄ (4 mol %). Catalyst C: Pd₂(dba)₃ (2 mol % complex), X-Phos 14 (8 mol %).

^cDiastereomeric ratios are reported for the isolated products. Diastereomeric ratios in parentheses were observed in crude reaction mixtures.

^dIsolated yield (average of two experiments).

^eThe reaction was conducted using 8 mol % PCy₃•HBF₄.