Table 1.

Reaction Optimization^a,b

			conversion ratio (2:3:1:4)b		product yieldb,c (%)
entry	arene	silver source	1 h	4 h	1 day
1d	-	Ag2CO3	66:34:0:0	25:40:35:0	>95 (1)
2	-	Ag2CO3	61:36:3:0	39:59:2:0	98 (3)
3	5a	Ag2CO3	53:45:2:0	17:78:5:0	>95 (3)
4	5b	Ag2CO3	70:2:2:0	26:70:1:0	>98 (3)e
5	5c	Ag2CO3	54:9:5:32	36:9:5:50	98 (4c)
6	5b	AgOTf	42:0:17:20	0:0:16:15	36 (4b)
7f	5b	AgOTf	0:0:32:42	0:0:52:33	54 (4b)
8f,g	5b	AgOTf	0:0:40:39	0:0:24:53	71 (4b)

^aReactions were carried out under argon with 2 (0.10 mmol) with arenes 5a-c(2.0 equiv), silver reagent [1.5 equiv in Ag(I)], and 30 mg of 4 Å molecular sieves in CDCl₃ (2.0 mL).

^bNMR ratios and yields determined for the crude reaction mixture by ¹⁹F NMR with C₆F₆ as the internal standard.

^cNMR yields determined for the crude reaction mixture by ¹H NMR with mesitylene as the internal standard.

^dReaction carried out without 4 Å molecular sieves.

^eThe reaction was also carried out at higher temperatures (up to 60 °C), and the formation of 4b was not observed.

^fReaction carried out in anhydrous Et₂O.

^gReaction carried out at 0.3 M.