Table 1.

Synthesis of carbazoles and analogues^a

entry	substrate	aryl triflate	CsF (equiv)	product	% isolated yield
1		1a	3.0		77
2	1	1a	5.0		66b
3	1	1b	3.0		61 (5:1)
4		1c	3.0		68
5	6	1a	3.0		69
6		1a	3.0		68
7		1a	3.0		72
8		1a	3.0		87
9	13	1c	3.0		85
10		1a	3.0		82
11	16	1c	3.0		71
12		1a	3.0		76c
13		1a	3.0		85
14	20	1c	3.0		85
15		1a	3.0		86
16	23	1c	3.0		85
17		1a	3.0		85
18	26	1c	3.0		85
19	26		3.0		62
20		1a	3.0		83 (1:1)
21		1a	3.0		66
22		1a	3.0		62

^aReaction conditions: 0.25 mmol of aryl iodide are allowed to react with 1.1 equiv of the aryl triflate and the number of equiv of CsF shown in the table in 4.0 mL of MeCN as the solvent at room temperature for 10 h, followed by the addition of 5 mol % Pd(OAc)₂ and 10 mol % PCy₃ and heating for 1 d at 100 °C .

^b2.4 Equiv of aryl triflate were emp loyed and the reaction was run at room temperature for 2 d, followed by the addition of 5 mol % Pd(OAc)₂ and 10 mol % PCy₃ and heating for 1 d at 100 °C.

^cThe reaction was run at room temperature for 1.5 d, followed by the addition of 5 mol % Pd(OAc)₂ and 10 mol % PCy₃ and heating for 1 d at 100 °C.