Table 4.

Reaction of Acrylic Acids with Arynes.^a

entry	R1	R2	R3	product	yieldb (%)
1	Me	H	H	30	84
2	H		H	31	85
3	H	nPr	H	32	82
4	H	NC(CH2)3	H	33	71
5	H	Me	Me	34	77
6	H		Me	35	64
7	Ph	H	H	36	56
8	H	Ph	H	37	74c
9	Me	Me	H	38	76d
10	Me	Ph	H	39	67e
11			H	40	78
12	H	CO2Me	H	41	0
13	H	Me	Me	42	53f
14	H	Ph	H	43	29c,g

^aReaction conditions: 0.25 mmol of the carboxylic acid, 1.5 equiv of aryne precursor and 4.0 equiv of CsF in 15 mL of THF were heated in a closed vial at 125 °C for 18 h. Then an additional 0.5 equiv of the aryne precursor and 1.0 equiv of CsF were added and the heating continued at 125 °C for 6 h.

^bIsolated yield.

^cThe yield includes the product obtained after base-induced cyclization of the o-hydroxyaryl ketone (see the Supporting Information).

^dThe E/Z ratio is ~1.8/1.

^eThe E/Z ratio is ~5.1/1.

^f4,5-Dimethoxy-2-(trimethylsilyl)phenyl triflate was used as the aryne precursor.

^g3,5-Dimethoxy-2-(trimethylsilyl)phenyl triflate was used as the aryne precursor.