钯催化串联Heck环化反应制备氮杂桥环化合物

doi:10.6023/cjoc202104059

摘要/Abstract

报道了一种钯催化分子内Heck环化串联反应. 该反应使用3-取代保护的吲哚酰胺衍生物作为原料, 碘化钯作为催化剂, 4-(二甲氨基)三苯基膦作为配体, 在乙腈和甲苯混合溶剂中发生串联反应, 以优良的收率合成了氮杂桥环化合物. 该反应具有良好的官能团兼容性和较高的合成效率, 为“一锅法”构建稠环化合物提供了一种简便的方法.

关键词: 钯催化剂, 分子内Heck串联环化反应, 氮杂桥环化合物, 一锅法

Palladium-catalyzed intramolecular Heck tandem cyclization reactions were developed. With palladium iodide as a catalyst and 4-(dimethylamino)triphenylphosphine as a ligand, 3-substituted indoleamide derivatives were converted to bridged N-heterocyclic products in good yields under simple reaction conditions. The tandem reactions are featured by efficient construction of fused ring compounds in one pot and good functional group compatibility.

Key words: palladium catalyst, intramolecular Heck cyclization, bridged N-heterocyclic compound

引用此文

李曼, 汪颖, 徐允河. 钯催化串联Heck环化反应制备氮杂桥环化合物[J]. 有机化学, 2021, 41(8): 3073-3082.

Man Li, Ying Wang, Yunhe Xu. Palladium-Catalyzed Tandem Heck Cyclization Reactions to Access the Bridged N-Heterocyclic Compounds[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3073-3082.

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参考文献 19

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Entry	Catalyst+Ligand	Additive (equiv.)	Base	Yield/%
1	Pd(OAc)₂+PPh₃	None	Na₂CO₃	10
2	Pd(OAc)₂+PPh₃	None	CsF	33
3	Pd(OAc)₂+PPh₃	None	Cs₂CO₃	35
4	Pd(OAc)₂+PPh₃	H₂O (7)	Cs₂CO₃	51
5	Pd(OAc)₂+L1	H₂O (7)	Cs₂CO₃	5
6	Pd(OAc)₂+L2	H₂O (7)	Cs₂CO₃	43
7	Pd(OAc)₂+L3	H₂O (7)	Cs₂CO₃	60
8	PdBr₂+L3	H₂O (7)	Cs₂CO₃	50
9	PdCl₂+L3	H₂O (7)	Cs₂CO₃	59
10	Pd(TFA)₂+L3	H₂O (7)	Cs₂CO₃	12
11	PdI₂+L3	H₂O (7)	Cs₂CO₃	75 (72^c)
12	Pd₂(dba)₃+L3	H₂O (7)	Cs₂CO₃	54
13	Pd(PPh₃)₄+L3	H₂O (7)	Cs₂CO₃	8
14^d	PdI₂+L3	H₂O (7)	Cs₂CO₃	16
15^e	PdI₂+L3	H₂O (7)	Cs₂CO₃	48
16	L3	H₂O (7)	Cs₂CO₃	0
17	PdI₂	H₂O (7)	Cs₂CO₃	12
18	PdI₂+L3	H₂O (7)	None	0

Entry	Catalyst+Ligand	Additive (equiv.)	Base	Yield/%
1	Pd(OAc)₂+PPh₃	None	Na₂CO₃	10
2	Pd(OAc)₂+PPh₃	None	CsF	33
3	Pd(OAc)₂+PPh₃	None	Cs₂CO₃	35
4	Pd(OAc)₂+PPh₃	H₂O (7)	Cs₂CO₃	51
5	Pd(OAc)₂+L1	H₂O (7)	Cs₂CO₃	5
6	Pd(OAc)₂+L2	H₂O (7)	Cs₂CO₃	43
7	Pd(OAc)₂+L3	H₂O (7)	Cs₂CO₃	60
8	PdBr₂+L3	H₂O (7)	Cs₂CO₃	50
9	PdCl₂+L3	H₂O (7)	Cs₂CO₃	59
10	Pd(TFA)₂+L3	H₂O (7)	Cs₂CO₃	12
11	PdI₂+L3	H₂O (7)	Cs₂CO₃	75 (72^c)
12	Pd₂(dba)₃+L3	H₂O (7)	Cs₂CO₃	54
13	Pd(PPh₃)₄+L3	H₂O (7)	Cs₂CO₃	8
14^d	PdI₂+L3	H₂O (7)	Cs₂CO₃	16
15^e	PdI₂+L3	H₂O (7)	Cs₂CO₃	48
16	L3	H₂O (7)	Cs₂CO₃	0
17	PdI₂	H₂O (7)	Cs₂CO₃	12
18	PdI₂+L3	H₂O (7)	None	0