Selective Synthesis of 3-Selenoindoles via Selenation of Indoles under Catalyst-Free Condition

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Dengpeng Xia, Qi Wu, Zhihua Cai, Guangfen Du. Selective Synthesis of 3-Selenoindoles via Selenation of Indoles under Catalyst-Free Condition[J]. Chinese Journal of Organic Chemistry, 2025, 45(1): 349-357.

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References 34

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Entry	Catalyst	Solvent	Time/h	Yield^b/%
1	K₂CO₃	CH₃CN	18	70
2	Cs₂CO₃	CH₃CN	18	49
3	NaHCO₃	CH₃CN	18	61
4	Na₂CO₃	CH₃CN	18	64
5	KOH	CH₃CN	18	76
6	PPh₃	CH₃CN	18	57
7	^tBuOK	CH₃CN	18	48
8	DBU	CH₃CN	18	70
9	TBD	CH₃CN	18	67
10	DBN	CH₃CN	18	79
1	Et₃N	CH₃CN	18	67
12	DIPEA	CH₃CN	18	76
13	DABCO	CH₃CN	18	69
14	—	CH₃CN	18	85
15	—	THF	18	77
16	—	DCM	18	86
17	—	DCE	18	78
18	—	MeOH	18	82
19	—	Toluene	18	46
20	—	1,4-Dioxane	18	53
21	—	DMF	18	51
22	—	DMSO	18	62
23	—	DME	18	78
24^c	—	DCM	18	83
25^d	—	DCM	18	86
26	—	DCM	6	73
27	—	DCM	12	83
28	—	DCM	24	99

Entry	Catalyst	Solvent	Time/h	Yield^b/%
1	K₂CO₃	CH₃CN	18	70
2	Cs₂CO₃	CH₃CN	18	49
3	NaHCO₃	CH₃CN	18	61
4	Na₂CO₃	CH₃CN	18	64
5	KOH	CH₃CN	18	76
6	PPh₃	CH₃CN	18	57
7	^tBuOK	CH₃CN	18	48
8	DBU	CH₃CN	18	70
9	TBD	CH₃CN	18	67
10	DBN	CH₃CN	18	79
1	Et₃N	CH₃CN	18	67
12	DIPEA	CH₃CN	18	76
13	DABCO	CH₃CN	18	69
14	—	CH₃CN	18	85
15	—	THF	18	77
16	—	DCM	18	86
17	—	DCE	18	78
18	—	MeOH	18	82
19	—	Toluene	18	46
20	—	1,4-Dioxane	18	53
21	—	DMF	18	51
22	—	DMSO	18	62
23	—	DME	18	78
24^c	—	DCM	18	83
25^d	—	DCM	18	86
26	—	DCM	6	73
27	—	DCM	12	83
28	—	DCM	24	99

无催化条件下吲哚选择性硒化制备3-硒代吲哚

Selective Synthesis of 3-Selenoindoles via Selenation of Indoles under Catalyst-Free Condition

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