Table 2.

Preparation of the Diarylalkynes ^a

entry	XR1	YR2	time (h)	temp (°C)	product	yield (%)
1	SMe	SeMe	24	25	9	80
2	SMe	OMe	6	60	10	90
3	SMe	CO2Me	14	25	11	98
4	SMe	CONHPh	1	25	-	-b
5	SMe	NMe2	24	25	-	-c
6	CO2Me	SeMe	10	60	12	87
7	CO2Me	CONH2	2	25	13	83
8	CO2Me	CONHPh	4	60	14	62d
9	CO2Me	NMe2	8	25	15	78
10	CO2Me	OMe	4	25	16	74
11	CO2Me	CHO	14	25	17	84
12	CO2Me	COMe	4	25	18	88
13	CO2Me	Ph	2	25	19	70
14	CONHPh	SMe	3	65	-	-b,e
15	CONHPh	SeMe	18	65	-	-c,e
16	NMe2	Ph	3	75	20	35
17	NMe2	Ph	2	110	20	74f
18	OMe	NMe2	24	25	21	70
19	OMe	CHO	7	25	22	80
20	OMe	OBn	8	60	23	72
21	OMe	Ph	2	25	24	94
22	CHO	NMe2	6	60	-	-b

^aAll reactions were run using 1 mmol of iodoarene and 1.2 equiv of alkyne, 2 mol % PdCl₂(PPh₃)₂, 1 mol % CuI, and 5 mL of Et₃N.

^bAn inseparable mixture was obtained.

^cThe desired compound was not observed.

^dFour mol % of CuI was used.

^eTwo milliliters of DMF were used to dissolve the alkyne.

^fThe reaction was carried out in toluene using a modified procedure; see the Supporting Information.