Rhodium(III)-Catalyzed Synthesis of CF3-1H-benzo[de][1,8]naph-thyridines via C—H Activation/Annulation of Benzimidates and CF3-Imidoyl Sulfoxonium Ylides

doi:10.6023/cjoc202306002

Abstract

A rhodium-catalyzed C—H activation/annulation domino reaction of benzimidates and CF₃-imidoyl sulfoxonium ylides has been achieved. This synthetic strategy has good functional groups tolerance and universality of substrates, and a series of trifluoromethyl-containing 1H-benzo[de][1,8]naphthyridines were synthesized in 22%~86% yields.

Key words: rhodium catalysis, benzimidate, trifluoromethyl, sulfoxonium ylide, benzo[de][1,8]naphthyridine

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Si Wen, Yuhao Ding, Qingyu Tian, Jin Ge, Guolin Cheng. Rhodium(III)-Catalyzed Synthesis of CF₃-1H-benzo[de][1,8]naph-thyridines via C—H Activation/Annulation of Benzimidates and CF₃-Imidoyl Sulfoxonium Ylides[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 291-300.

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Fig. & Tab. 6

References 16

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Entry	Solvent	Base	Additive	Yield^b/%
1	DCE	NaOAc	AgSbF₆	54
2	DMF	NaOAc	AgSbF₆	0
3	DMSO	NaOAc	AgSbF₆	0
4	THF	NaOAc	AgSbF₆	44
5	HFIP	NaOAc	AgSbF₆	58
6	Toluene	NaOAc	AgSbF₆	74
7	Toluene	Na₂CO₃	AgSbF₆	20
8	Toluene	^tBuONa	AgSbF₆	0
9	Toluene	KHCO₃	AgSbF₆	58
10	Toluene	KOAc	AgSbF₆	18
11	Toluene	Cs₂CO₃	AgSbF₆	0
12	Toluene	CsOAc	AgSbF₆	48
13	Toluene	Li₂CO₃	AgSbF₆	46
14	Toluene	LiOAc	AgSbF₆	58
15	Toluene	—	AgSbF₆	70
16	Toluene	NaOAc	AgOAc	32
17	Toluene	NaOAc	—	0
18^d	Toluene	NaOAc	AgSbF₆	68
19^e	Toluene	NaOAc	AgSbF₆	77
20^e^,^f	Toluene	NaOAc	AgSbF₆	80 (75)^c
21^e^,^g	Toluene	NaOAc	AgSbF₆	72
22^e^,^h	Toluene	NaOAc	AgSbF₆	54
23^e^,ⁱ	Toluene	NaOAc	AgSbF₆	Trace

Entry	Solvent	Base	Additive	Yield^b/%
1	DCE	NaOAc	AgSbF₆	54
2	DMF	NaOAc	AgSbF₆	0
3	DMSO	NaOAc	AgSbF₆	0
4	THF	NaOAc	AgSbF₆	44
5	HFIP	NaOAc	AgSbF₆	58
6	Toluene	NaOAc	AgSbF₆	74
7	Toluene	Na₂CO₃	AgSbF₆	20
8	Toluene	^tBuONa	AgSbF₆	0
9	Toluene	KHCO₃	AgSbF₆	58
10	Toluene	KOAc	AgSbF₆	18
11	Toluene	Cs₂CO₃	AgSbF₆	0
12	Toluene	CsOAc	AgSbF₆	48
13	Toluene	Li₂CO₃	AgSbF₆	46
14	Toluene	LiOAc	AgSbF₆	58
15	Toluene	—	AgSbF₆	70
16	Toluene	NaOAc	AgOAc	32
17	Toluene	NaOAc	—	0
18^d	Toluene	NaOAc	AgSbF₆	68
19^e	Toluene	NaOAc	AgSbF₆	77
20^e^,^f	Toluene	NaOAc	AgSbF₆	80 (75)^c
21^e^,^g	Toluene	NaOAc	AgSbF₆	72
22^e^,^h	Toluene	NaOAc	AgSbF₆	54
23^e^,ⁱ	Toluene	NaOAc	AgSbF₆	Trace

铑(III)催化苯甲亚胺酸乙酯和CF₃-亚胺氧锍叶立德C—H 活化/环化反应合成CF₃-1H-苯并[de][1,8]萘吡啶

Rhodium(III)-Catalyzed Synthesis of CF₃-1H-benzo[de][1,8]naph-thyridines via C—H Activation/Annulation of Benzimidates and CF₃-Imidoyl Sulfoxonium Ylides

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铑(III)催化苯甲亚胺酸乙酯和CF3-亚胺氧锍叶立德C—H 活化/环化反应合成CF3-1H-苯并[de][1,8]萘吡啶