Palladium-Catalyzed Tandem Heck Cyclization Reactions to Access the Bridged N-Heterocyclic Compounds

doi:10.6023/cjoc202104059

Abstract

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

Cite this article

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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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

钯催化串联Heck环化反应制备氮杂桥环化合物