. Author manuscript; available in PMC: 2008 Oct 1.

Published in final edited form as: J Org Chem. 2006 Jan 6;71(1):62–69. doi: 10.1021/jo051549p

TABLE 2.

Synthesis of 3-Iodoindoles.^a

entry		time (h)	product		isolated yield (%)
1	2	2		29	100
2	3	2		30	96
3	4	2		31	94
4	5	2		32	85
5	6	4		33	?
6	7	4		34	86
7	8	4		35	73
8	10	0.5		36	100
9	11	0.5		37	95
10	12	0.5		38	100
11	14	0.5		39	100
12	15	0.5		40	100
13	16	0.5		41	98
14	18	2		42	84
15	19	2		43	84
16	20	2		44	100
17	22	0.5	R = n-Bu (45)R = Me (46)		98(72:28) ^b(45:46)
18	23	0.5	R = n-Bu (47)R = Me (48)		84(62:38) ^b(47:48)
19	24	0.5	R = n-Bu (49)R = Me (50)		92(66:34) ^b(49:50)
20	26	2	R = Me (27) (51)		50(90:10) ^b(27:51)
21	28	1	R = Ph (52)R = Me (27)		80(100:0) ^b(52:27)

All reactions were run with 0.25 mmol of the alkyne and 2 equiv of I₂ in 5 mL of CH₂Cl₂ at 25 °C, followed by the addition of 5 mL of satd aq Na₂S₂O₃ to remove the excess I₂.

Ratio of the products shown immediately below.