Table 3.

Results of the competitive cyclizations ^a

Entry	Substrate	Electrophile	Time (h)	product(s)	Yield (%)
1		1.1 I2	0.16		82b
2		1.2 I2	1		96
3		1.1 I2	0.5		91c
4		1.2 I2	1		98d
5	12	1.2 ICl		29	93d
6		1.2 I2	1		93
					7
7	11	1.2 ICl	0.5	30 +	93
				31	7
8	11	1.5 PhSeCl	1		56e
					44e
9		1.2 I2	1		95
10		2 PhSeCl	3		70
11		1.2 I2	1	-	-f
12	13	3 I2	1	-	-f,g
13		1.2 I2	1		45
					18
14	14	1.2 ICl	1	36+	35
				37	30
15		1.2 I2	1.5		57h
16		1.2 I2	1		98
17	16	2 ICl	0.5	39	96
18	16	1.5 PhSeCl	0.5	E = SePh 40	95
19		1.2 I2	2	-	-i
20	17	1.2 ICl	0.5		25j
21	17	1.2 I2, 1.2 MeOH/1.0 K2CO3	10		82k
					12
22		1.2 I2	1	-	-f
23	18	1.2 ICl	0.5	-	-f
24	18	1.2 I2, 1.2 MeOH/1.0 K2CO3	2	-	-f
25		2 I2	3		4:1l
26	23	1.2 ICl	3	43 + 44	6:1l
27		2 I2	3		95m
28		2 I2	2		78
29	20	1.2 ICl	0.5	-	-f
30	20	1.2 NBS	1	-	-f
31		2 ICl	3		90
32		2 I2	3	-	-f
33	24	1.2 ICl	0.5		49e
					33e
34		6 I2	2		89d
35	26	1.2 ICl	1	-	-d,n

^aUnless otherwise stated, all reactions have been carried out on a 0.25 mmol scale in 5 ml of methylene chloride at room temperature. All yields are isolated yields after column chromatography.

^bA small amount of the corresponding benzothiophene product (~7%) was observed by GC-MS analysis; however, it could not be isolated.

^cThis result has previously been reported in the literature (see reference ^8a).

^dThis reaction hasf been carried out on a 0.10 mmol scale.

^eThe reported yield is the average of two runs.

^fThis reaction resulted in a complex mixture of unidentifiable products.

^gMeCN was used as the reaction solvent and 3 equiv of NaHCO₃ were added as a base.

^hThe corresponding indole (~8%) was also observed by GC-MS analysis. However, it could not be isolated.

ⁱNo reaction occurred; the starting material was recovered. A complex mixture was obtained upon longer reaction.

^jThis was the only isolated product. The rest of the product mixture was complex and inseparable.

^kThis product decomposed quickly; see the Supporting Information for details.

^lAn inseparable complex mixture was obtained. This ratio is based on GC-MS data.

^mThis result has previously been reported in the literature (see reference ^3b).

ⁿAn alkyne ICl addition product whose structure is similar to compound 49 in entry 34 was obtained.