Table 2. Cyclocarbonylative Sonogashira Reactions of 2-Ethynylbenzamide 1 with Iodoarenes 2 Performed in CH₂Cl₂.

						selectivityc (%)
entrya	Ar	2	t (h)	conversionb (%)	3, 4	3	4
1	Ph	a	4	80	a	57 (34)	43 (21)
2	4-OMePh	b	4	79	b	55 (38)	45 (30)
3	4-OMePh	b	8	84	b	56	44
4	4-OMePh	b	24	100	b	58	42
5d	2-OMePh	c	24	73	c	50 (37)	50 (29)
6	4-ClPh	d	4	90	d	58 (32)	42 (37)
7	4-CNPh	e	4	86	e	36 (15)	64 (44)

^aAll reactions were carried with 2-ethynylbenzamide 1 (1.0 mmol), iodoarene 2 (1.0 mmol), CO (20 atm), PdCl₂(PPh₃)₂ (0.4 mol %), Et₃N (1.5 mL), and CH₂Cl₂ (4.0 mL) at 100 °C, unless otherwise stated.

^bConversion was determined by ¹H NMR peak integration on the crude product.

^cSelectivity was estimated by ¹H NMR spectroscopy; isolated yields of pure products are reported in parentheses.

^dReaction performed with 1 mol % of PdCl₂(PPh₃)₂.