Table 4. Cyclocarbonylative Sonogashira Reactions of N-(4-Chlorophenyl)-2-ethynylbenzamide 6 with Iodoarenes 2.

						selectivityc (%)
entrya	Ar	2	t (h)	conversionb (%)	7	(E)-7	(Z)-7
1	Ph	a	4	100	a	89 (66)	11 (6)
2d	Ph	a	24	84	a	90	10
3	4-OMePh	b	4	100	b	88 (69)	12 (10)
4	2-OMePh	c	4	100	c	93 (74)	7 (3)
5	4-ClPh	d	4	100	d	84f (51)	10f (7)
6e	4-ClPh	d	4	100	d	86f	10f
7	1-Napht	f	4	100	f	89 (69)	11 (5)
8	4-MePh	g	4	100	g	90 (67)	10 (7)
9	2-MePh	h	4	100	h	88 (60)	12 (5)

^aAll reactions were carried with N-(4-chlorophenyl)-2-ethynylbenzamide 6 (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 at 50 °C.

^eReaction performed under 40 atm of CO.

^fThe remainder of the product was (Z)-3-(4-chlorobenzylidene)-2-(4-chlorophenyl)isoindolin-1-one 8.