Table 2. Synthesis of Diverse Polycyclic Heterocycles Using the Catalytic C–H Alkylation.

Entry	Substrate	Product	yield(%)a
1b	27: X = Br, R = H	28: R = H	54
2	29: X = I, R = H		82
3	30: X = I, R = CF3	31: R = CF3	70
4	32: X = I, R = OMe	33: R = OMe	66
5	34: X = I, R = B(pin)	35: R = B(pin)	72
6	36: X = I, R = C(O)Me	37: R = C(O)Me	77
7			57
8			80
9	40: R = CF3	41: R = CF3	81: (2.4:1 o:p)
10	42: R = Me	43: R = Me	91c(2.0:1 o:p)
11			57
12			61
13	48: R = H	49: R = H	51c
14	50: R = Me	51: R = Me	71c
15	52: R = H	53: R = H	70c
16	54: R = Me	55: R = Me	90c
17	56: R = H	57: R = H	64c
18	58: R = Me	59: R=Me	95c

All reactions were performed with [substrate]₀ = 0.5 M in dioxane at 100 °C with 10 mol % Pd(PPh₃)₄ and 2 equiv K₃PO₄ as base.

^aIsolated yields.

^bThe reaction was performed at 130 °C in PhtBu.

^cCalculated by ¹H NMR spectroscopy of crude reaction mixtures using an internal standard.