Silver-Catalyzed 5-Exo-dig Cyclization Reaction of ortho-Hydroxyphenylpropargyl Alcohols to 2-Methylene-2,3-dihydrobenzofuran

doi:10.6023/cjoc202310023

Abstract

2-Methylene-2,3-dihydrobenzofuran derivatives, as one of the core skeletons of various natural products and drugs, are of great significance in finding new methods for effectively synthesizing 2-methylene-2,3-dihydrobenzofuran from easily available raw materials. Herein, a novel silver-catalyzed 5-exo-dig cyclization reaction of orth-hydroxyphenyl alkynyl alcohols has been developed, providing an efficient and modular method for the construction of 2-methylene-2,3-dihydrobenzofuran. Featuring the advantages of mild conditions, simple operation, and high efficiency, the reaction requires the utilization of 2 mol% of silver carbonate as a catalyst and 5 mol% of isocyanide as a ligand at room temperature.

Key words: silver, isocyanide, cyclization, propargylic alcohol, benzofuran

Cite this article

Miao Feng, Lanlan Lü, Yijia Guo, Jianquan Liu, Xiangshan Wang. Silver-Catalyzed 5-Exo-dig Cyclization Reaction of ortho-Hydroxyphenylpropargyl Alcohols to 2-Methylene-2,3-dihydrobenzofuran[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1218-1225.

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Entry	[M]	Solvent	Ligand	Temp./℃		Yield^b/%
1	Ag₂CO₃	1,4-Dioxane	L1	40		75
2	Ag₂CO₃	DMF	L1	40		64
3	Ag₂CO₃	DMSO	L1	40		27
4	Ag₂CO₃	Toluene	L1	40		49
5	Ag₂CO₃	MeCN	L1	40		38
6	Ag₂CO₃	DCE	L1	40		58
7	AgOAc	1,4-Dioxane	L1	40		60
8	AgF	1,4-Dioxane	L1	40		45
9	Ag₂O	1,4-Dioxane	L1	40	61
10	AgOTf	1,4-Dioxane	L1	40	0
11	Ag₃PO₄	1,4-Dioxane	L1	40	0
12	AgBF₄	1,4-Dioxane	L1	40	0
13	Pd(OAc)₂	1,4-Dioxane	L1	40	0
14	CuI	1,4-Dioxane	L1	40	0
15	Ag₂CO₃	1,4-Dioxane	L2	40	28
16	Ag₂CO₃	1,4-Dioxane	L3	40	36
17	Ag₂CO₃	1,4-Dioxane	L4	40	43
18	Ag₂CO₃	1,4-Dioxane	L1	r.t.	83
19	Ag₂CO₃	1,4-Dioxane	L1	60	71
20^c	—	1,4-Dioxane	L1	60	0
21^d	Ag₂CO₃	1,4-Dioxane	—	r.t.	0
22^e	Ag₂CO₃	1,4-Dioxane	L1	r.t.	23
23^e	Ag₂CO₃	1,4-Dioxane	L5	r.t.	90
24^e	Ag₂CO₃	1,4-Dioxane	L6	r.t.	86

Entry	[M]	Solvent	Ligand	Temp./℃		Yield^b/%
1	Ag₂CO₃	1,4-Dioxane	L1	40		75
2	Ag₂CO₃	DMF	L1	40		64
3	Ag₂CO₃	DMSO	L1	40		27
4	Ag₂CO₃	Toluene	L1	40		49
5	Ag₂CO₃	MeCN	L1	40		38
6	Ag₂CO₃	DCE	L1	40		58
7	AgOAc	1,4-Dioxane	L1	40		60
8	AgF	1,4-Dioxane	L1	40		45
9	Ag₂O	1,4-Dioxane	L1	40	61
10	AgOTf	1,4-Dioxane	L1	40	0
11	Ag₃PO₄	1,4-Dioxane	L1	40	0
12	AgBF₄	1,4-Dioxane	L1	40	0
13	Pd(OAc)₂	1,4-Dioxane	L1	40	0
14	CuI	1,4-Dioxane	L1	40	0
15	Ag₂CO₃	1,4-Dioxane	L2	40	28
16	Ag₂CO₃	1,4-Dioxane	L3	40	36
17	Ag₂CO₃	1,4-Dioxane	L4	40	43
18	Ag₂CO₃	1,4-Dioxane	L1	r.t.	83
19	Ag₂CO₃	1,4-Dioxane	L1	60	71
20^c	—	1,4-Dioxane	L1	60	0
21^d	Ag₂CO₃	1,4-Dioxane	—	r.t.	0
22^e	Ag₂CO₃	1,4-Dioxane	L1	r.t.	23
23^e	Ag₂CO₃	1,4-Dioxane	L5	r.t.	90
24^e	Ag₂CO₃	1,4-Dioxane	L6	r.t.	86

银催化邻羟基苯基炔丙醇5-exo-dig环化反应构筑2-亚甲基-2,3-二氢苯并呋喃-3-醇