邻亚甲醌与硫叶立德反应合成2,3-二取代苯并二氢呋喃化合物

doi:10.6023/cjoc202307019

摘要/Abstract

发展了一种简便有效的通过邻甲亚醌与硫叶立德反应合成苯并二氢呋喃化合物的方法. 在二氯甲烷中和二异丙基乙基胺存在下, 反应能够在室温下1 h内完成, 以良好至优秀的收率得到反式-2,3-二取代二氢苯并呋喃产物. 反应能够扩大到克级规模, 产物能够转化为潜在生物活性的苯并呋喃衍生物, 并推测了可能的反应机理,

关键词: 苯并二氢呋喃, 邻亚甲醌, 硫叶立德, [4＋1]环加成, 碱催化

A facile and efficient approach to dihydrobenzofurans from sulfur ylides and o-quinone methides (o-QMs) was developed. In most cases, the reaction could be completed in the presence of N,N-diisopropylethylamine (DIPEA) in CH₂Cl₂ at room temperature within 1 h, providing trans-2,3-disubstitiuted dihydrobenzofurans in good to excellent yields. The reaction could expand to a scale of grams, and the products could be converted into the potentially bioactive benzofuran derivatives. The plausible mechanism is proposed.

Key words: dihydrobenzofuran, o-quinone methides, sulfur ylide, [4＋1] cycloaddition, base-catalysis

引用此文

李梦竹, 孟博莹, 兰文捷, 傅滨. 邻亚甲醌与硫叶立德反应合成2,3-二取代苯并二氢呋喃化合物[J]. 有机化学, 2024, 44(1): 195-203.

Mengzhu Li, Boying Meng, Wenjie Lan, Bin Fu. Synthesis of 2,3-Disubstituted Dihydrobenzofurans from o-Quinone Methides and Sulfur Ylides[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 195-203.

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参考文献 18

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Entry	Solvent	Base	T/℃	Time/h	Yield^b/%
1	CH₃CN	K₂CO₃	r.t.	6	75
2	THF	K₂CO₃	r.t.	6	85
3	CHCl₃	K₂CO₃	r.t.	6	86
4	CH₂Cl₂	K₂CO₃	r.t.	6	91
5	Dioxane	K₂CO₃	r.t.	12	68
6	Acetone	K₂CO₃	r.t.	16	73
7	Toluene	K₂CO₃	r.t.	24	85
8	CH₃OH	K₂CO₃	r.t.	24	—
9	CH₂Cl₂	Li₂CO₃	r.t.	6	93
10	CH₂Cl₂	Na₂CO₃	r.t.	6	89
11	CH₂Cl₂	Cs₂CO₃	r.t.	12	91
12	CH₂Cl₂	t-BuOK	r.t.	12	30
13	CH₂Cl₂	Et₃N	r.t.	1	85
14	CH₂Cl₂	DIEPA	r.t.	1	97
15	CH₂Cl₂	DIEPA	0	6	83
16	CH₂Cl₂	DIEPA	40	1	90

Entry	Solvent	Base	T/℃	Time/h	Yield^b/%
1	CH₃CN	K₂CO₃	r.t.	6	75
2	THF	K₂CO₃	r.t.	6	85
3	CHCl₃	K₂CO₃	r.t.	6	86
4	CH₂Cl₂	K₂CO₃	r.t.	6	91
5	Dioxane	K₂CO₃	r.t.	12	68
6	Acetone	K₂CO₃	r.t.	16	73
7	Toluene	K₂CO₃	r.t.	24	85
8	CH₃OH	K₂CO₃	r.t.	24	—
9	CH₂Cl₂	Li₂CO₃	r.t.	6	93
10	CH₂Cl₂	Na₂CO₃	r.t.	6	89
11	CH₂Cl₂	Cs₂CO₃	r.t.	12	91
12	CH₂Cl₂	t-BuOK	r.t.	12	30
13	CH₂Cl₂	Et₃N	r.t.	1	85
14	CH₂Cl₂	DIEPA	r.t.	1	97
15	CH₂Cl₂	DIEPA	0	6	83
16	CH₂Cl₂	DIEPA	40	1	90

Entry	R²	Product	Time/h	Yield^b/%	dr^c
1	4-ClC₆H₄	3ab	1	88	>19∶1
2	4-BrC₆H₄	3ac	1	80	>19∶1
3	4-CNC₆H₄	3ad	1	89	>19∶1
4	4-CF₃C₆H₄	3ae	1	86	>19∶1
5	4-CH₃C₆H₄	3af	1	98	>19∶1
6	3-MeOC₆H₄	3ag	1	87	>19∶1
7	3-FC₆H₄	3ah	1	75	>19∶1
8	3-O₂NC₆H₄	3ai	1	96	>19∶1
9	2-FC₆H₄	3aj	1	81	>19∶1
10	2-HOC₆H₄	3ak	1	92	>19∶1
11	2-Naphthyl	3al	1	83	>19∶1
12	2-Furyl	3am	6	78	>19∶1
13	2-Thienyl	3an	8	87	>19∶1
14	Cyclopropyl	3ao	1	80	>19∶1
15	t-Bu	3ap	1	87	>19∶1
16	Adamantyl	3aq	1	81	>19∶1

Entry	R²	Product	Time/h	Yield^b/%	dr^c
1	4-ClC₆H₄	3ab	1	88	>19∶1
2	4-BrC₆H₄	3ac	1	80	>19∶1
3	4-CNC₆H₄	3ad	1	89	>19∶1
4	4-CF₃C₆H₄	3ae	1	86	>19∶1
5	4-CH₃C₆H₄	3af	1	98	>19∶1
6	3-MeOC₆H₄	3ag	1	87	>19∶1
7	3-FC₆H₄	3ah	1	75	>19∶1
8	3-O₂NC₆H₄	3ai	1	96	>19∶1
9	2-FC₆H₄	3aj	1	81	>19∶1
10	2-HOC₆H₄	3ak	1	92	>19∶1
11	2-Naphthyl	3al	1	83	>19∶1
12	2-Furyl	3am	6	78	>19∶1
13	2-Thienyl	3an	8	87	>19∶1
14	Cyclopropyl	3ao	1	80	>19∶1
15	t-Bu	3ap	1	87	>19∶1
16	Adamantyl	3aq	1	81	>19∶1

Entry	R¹	Product	Time/h	Yield^b/%	dr^c
1	Ph	3ba	1	55	>19∶1
2	4-CH₃C₆H₄	3ca	1	68	>19∶1
3	4-MeOC₆H₄	3da	12	67	>19∶1
4	4-FC₆H₄	3ea	1	85	>19∶1
5	4-ClC₆H₄	3fa	1	85	>19∶1
6	4-BrC₆H₄	3ga	1	83	>19∶1
7	3-MeC₆H₄	3ha	1	68	>19∶1
8	2-MeOC₆H₄	3ia	12	52	>19∶1
9	2-Thienyl	3ja	1	24	>19∶1