Table 1. Cyclocarbonylative Sonogashira Coupling Reactions of 2-Iodophenol (1a) with Phenylacetylene (2a) by C1^a,b.

							selectivity (%)c
No	C1 mol %	base	solvent	T (°C)	time (h)	conv. (%)c	3aa (%)d	4aa (%)d
1	1.0	Et2NH	Et2NH	RT	16	traces	traces	traces
2	1.0	Et2NH	Et2NH	80	16	59.5	100 (55)
3	1.0	Et2NH	Et2NH	100	16	85.5	100 (82)
4	1.0	Et3N	Et3N	80	16	85	43 (34)	57 (45)
5	1.0	Et3N	Et3N	100	16	100	34 (30)	66 (63)
6	1.0	Et3N	THF	80	16	69	40 (25)	60 (38)
7	1.0	Et3N	THF	100	16	93	36 (30)	64 (56)
8	1.0	Et2NH	THF	80	16	68	100 (64)
9	1.0	Et2NH	THF	100	16	84.5	100 (81)
10	1.0	K2CO3	THF	100	16	96	38 (33)	62 (57)
11	1.0	Et2NH	Toluene	100	16	97	93 (88)	7
12	0.5	Et2NH	THF	100	16	80	100 (77)
13	0.5	Et2NH	DMF	100	16	98	96 (92)	4
14	0.5	Et2NH	DMF	80	16	83	100 (81)
15	0.5	Et2NH	DMF	50	16	38	100 (35)
16	0.5	Et2NH	DMF	100	12	76	100 (72)
17	0.5	Et2NH	DMF	100	6	49	100 (46)
18	0.5	Et2NH	THF	100	16	72	100 (70)
19	0.5	Et2NH	Toluene	100	16	82	95 (76)	5
20	0.5	Et2NH	Et2NH	100	16	79	100 (76)
21	0.5	K2CO3	DMF	100	16	97	70 (65)	30 (27)
22	0.5	Et3N	DMF	100	16	95	60 (54)	40 (35)

^aOptimization of reaction conditions.

^bReaction conditions: C1 (mol %), 2-iodophenol (0.5 mmol), phenylacetylene (0.6 mmol), base (1.0 mmol), solvent (2.5 mL), and CO (100 psi), 100 °C.

^cDetermined by GC and GC–MS.

^dIsolated yield.