Table 1.

Facile N-Arylation of Aromatic Amines^a

entry	amine	silylaryl triflate (equiv)	CsF (equiv)	time (h)	product	% isolated yield
1		1a (1.1)	2.0	10		92
2		1b (1.1)	2.0	10		94
3		1a (1.1)	2.0	10		85
4		1a (1.1)	2.0	10		90
5		1a (1.1)	2.0	10		94
6		1a (1.1)	2.0	10		94
7		1a (1.1)	2.0	10		95
8		1a (1.1)	2.0	10		89b
9		1a (1.1)	2.0	10		91
10		1a (1.1)	2.0	10		92
11		1a (1.1)	2.0	10		91
12		1a (1.1)	2.0	10		77
13		1a (1.1)	2.0	10		90
14		1a (1.1)	2.0	5		96
15		1c (1.1)	2.0	10		97
16		1d (1.1)	2.0	5		94 (1:1)
17		1a (1.1)	2.0	5		97
18		1a (1.1)	2.0	5		97
19		1a (1.1)	2.0	5		97
20		1a (2.4)	4.0	72		98
21		1b (2.4)	4.0	72		94
22		1c (2.4)	4.0	72		93
23		1a (2.4)	4.0	72		100
24		1a (2.4)	4.0	72		81c
25		1a (2.4)	4.0	72		55d
26		1a (1.2)	2.0	24		76
27		1a (3.6)	6.0	72		81
28		1a (1.2)	2.0	24		92 (1 : 3.5)

^aAll reactions were run under the following reaction conditions, unless otherwise specified: 0.25 mmol of amine and the indicated amount of silylaryl triflate and CsF were stirred in 4 mL of MeCN at room temperature.

^bA 4% yield of the diarylated product was obtained.

^cOnly monoarylated product was obtained.

^dA 40% yield of monoarylated product was obtained.