ICl催化氨基香豆素衍生物Csp2—H芳(烷)硒化反应研究

doi:10.6023/cjoc202106055

摘要/Abstract

有机硒杂环化合物由于其独特的生物活性, 在有机化学和药物合成中具有广泛应用. 众多关于有机硒杂环化合物的合成方法被相继报道, 但这些方法均存在一定不足. 报道了ICl催化下香豆素衍生物与二芳(烷)二硒醚在室温下的反应, 高效制备了一系列3-芳(烷)硒基香豆素衍生物. 该方法也适用于其他杂环化合物C_sp2—Se键构建. 与已有方法相比, 本方法具有反应条件温和, 底物适用范围广等优点, 为有机硒杂环化合物的制备提供了方法.

关键词: 碘鎓催化芳(烷)硒化, C_sp2—Se键构建, 杂环化合物, 二芳(烷)基二硒醚

Owing to their special biological activities, organic selenium heterocyclic compounds have widely applications in organic chemistry and drug synthesis. A series of methods for the synthesis of organoselenide heterocyclic compounds have been reported, however, shortcomings still exist. In this paper, an effective method for the synthesis of 3-aryl(alkyl)selenylcoumarin derivatives via the ICl-catalyzed selenation of coumarins with diaryl(alkyl)diselenide at room temperature is reported. In addition, this method is also suitable for the construction of C_sp2—Se bonds of other heterocyclic compounds. Compared to previous methods, this method has the advantages of mild conditions and wide functional groups tolerance, providing a general pathway to organoselenide heterocyclic compounds.

Key words: Iodine cation-catalyzed selenation, Construction of C_sp2—Se, Heterocyclic compounds, Diaryl(alkyl)diselenides

引用此文

何树华, 张行, 吴红谕, 周诗雨, 肖垚, 游贤会, 陈锦杨. ICl催化氨基香豆素衍生物C_sp2—H芳(烷)硒化反应研究[J]. 有机化学, 2021, 41(11): 4378-4383.

Shuhua He, Hang Zhang, Hongyu Wu, Shiyu Zhou, Yao Xiao, Xianhui You, Jinyang Chen. ICl-Catalyzed C_sp2—H Selenation of Aminocoumarin Derivatives[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4378-4383.

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Entry	Cat. (mol%)	Solvent	Temp./℃	Time/h	Yield^b/%
1	ICl (50)	DMSO	r.t.	12	90
2	ICl (40)	DMSO	r.t.	12	90
3	ICl (30)	DMSO	r.t.	12	90
4	ICl (20)	DMSO	r.t.	12	90
5	ICl (10)	DMSO	r.t.	12	86
6	ICl (5)	DMSO	r.t.	12	63
7	I₂ (20)	DMSO	r.t.	12	62
8	None	DMSO	r.t.	12	N.D.^c
9	ICl (20)	DMF	r.t.	12	75
10	ICl (20)	DMA	r.t.	12	81
11 12 13 14 15 16	ICl (20) ICl (20) ICl (20) ICl (20) ICl (20) ICl (20)	THF Toluene DCM 1,4-Dioxane DMSO DMSO	r.t. r.t. r.t. r.t. 50 80	12 12 12 12 12 12	64 59 26 69 90 85
17	ICl (20)	DMSO	80	6	73
18	ICl (20)	DMSO	r.t.	16	90
19	ICl (20)	DMSO	r.t.	8	85
20^d	ICl (20)	DMSO	r.t.	12	90
21^e	ICl (20)	DMSO	r.t.	12	75

Entry	Cat. (mol%)	Solvent	Temp./℃	Time/h	Yield^b/%
1	ICl (50)	DMSO	r.t.	12	90
2	ICl (40)	DMSO	r.t.	12	90
3	ICl (30)	DMSO	r.t.	12	90
4	ICl (20)	DMSO	r.t.	12	90
5	ICl (10)	DMSO	r.t.	12	86
6	ICl (5)	DMSO	r.t.	12	63
7	I₂ (20)	DMSO	r.t.	12	62
8	None	DMSO	r.t.	12	N.D.^c
9	ICl (20)	DMF	r.t.	12	75
10	ICl (20)	DMA	r.t.	12	81
11 12 13 14 15 16	ICl (20) ICl (20) ICl (20) ICl (20) ICl (20) ICl (20)	THF Toluene DCM 1,4-Dioxane DMSO DMSO	r.t. r.t. r.t. r.t. 50 80	12 12 12 12 12 12	64 59 26 69 90 85
17	ICl (20)	DMSO	80	6	73
18	ICl (20)	DMSO	r.t.	16	90
19	ICl (20)	DMSO	r.t.	8	85
20^d	ICl (20)	DMSO	r.t.	12	90
21^e	ICl (20)	DMSO	r.t.	12	75