镍催化三氟甲基取代烯烃与烷基甲磺酸酯的烯丙位脱氟交叉亲电偶联

doi:10.6023/cjoc202603041

摘要/Abstract

基于镍催化的还原体系, 成功发展了三氟甲基取代烯烃与二级烷基甲磺酸酯的分子间烯丙位脱氟亲电交叉偶联反应, 发展了一种以醇类衍生物为亲电烷基来源、直接且高效构建偕二氟烯烃的新方法. 该反应采用原位(拟)卤素交换策略, 在碘化钠作用下将烷基甲磺酸酯原位转化为高活性的烷基碘物种, 从而顺利进入后续的催化循环.

关键词: 碳氟键断裂, 碳氧键断裂, 偕二氟烯烃, 交叉亲电偶联, 镍催化

A nickel-catalyzed reductive system that enables an intermolecular allylic defluorinative cross-electrophile coupling between trifluoromethyl-substituted alkenes and secondary alkyl mesylates is developed. It provides a direct and efficient method for constructing gem-difluoroalkenes, using alcohol-derived substrates as electrophilic alkyl sources. The reaction proceeds via an in situ (pseudo)halide-exchange strategy, in which sodium iodide converts alkyl mesylates into highly reactive alkyl iodide species, thereby enabling their smooth participation in the subsequent catalytic cycle.

Key words: C—F bond cleavage, C—O bond cleavage, gem-difluoroalkene, cross-electrophile coupling, nickel catalysis

引用此文

房毅, 王川. 镍催化三氟甲基取代烯烃与烷基甲磺酸酯的烯丙位脱氟交叉亲电偶联[J]. 有机化学, 2026, 46(7): 2743-2750.

Yi Fang, Chuan Wang. Nickel-Catalyzed Allylic Defluorinative Cross-Electrophile Coupling of Trifluoromethyl-Substituted Alkenes with Alkyl Mesylates[J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2743-2750.

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参考文献 14

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Entry	Ln	Precatalyst	Solvent (V∶V)	Yield^b/%	Entry	Ln	Precatalyst	Solvent (V∶V)	Yield^b/%
1	L1	Ni(dme)Br₂	THF/DMA (4∶1)	38	11	L7	Ni(dme)Br₂	THF/DMA (1∶1)	49
2	L2	Ni(dme)Br₂	THF/DMA (4∶1)	41	12	L7	Ni(dme)Br₂	THF/DMA (1∶4)	69
3	L3	Ni(dme)Br₂	THF/DMA (4∶1)	24	13	L7	NiBr₂	THF/DMA (1∶4)	58
4	L4	Ni(dme)Br₂	THF/DMA (4∶1)	Trace	14	L7	NiCl₂	THF/DMA (1∶4)	52
5	L5	Ni(dme)Br₂	THF/DMA (4∶1)	40	15	L7	Ni(OTf)₂	THF/DMA (1∶4)	24
6	L6	Ni(dme)Br₂	THF/DMA (4∶1)	Trace	16	L7	Ni(acac)₂	THF/DMA (1∶4)	40
7	L7	Ni(dme)Br₂	THF/DMA (4∶1)	58	17^c	L7	Ni(dme)Br₂	THF/DMA (1∶4)	90
8	L7	Ni(dme)Br₂	THF	47	18^c^,^d	L7	Ni(dme)Br₂	THF/DMA (1∶4)	0
9	L7	Ni(dme)Br₂	DMA	34	19^c^,^e	L7	Ni(dme)Br₂	THF/DMA (1∶4)	81
10	L7	Ni(dme)Br₂	MeCN	23

Entry	Ln	Precatalyst	Solvent (V∶V)	Yield^b/%	Entry	Ln	Precatalyst	Solvent (V∶V)	Yield^b/%
1	L1	Ni(dme)Br₂	THF/DMA (4∶1)	38	11	L7	Ni(dme)Br₂	THF/DMA (1∶1)	49
2	L2	Ni(dme)Br₂	THF/DMA (4∶1)	41	12	L7	Ni(dme)Br₂	THF/DMA (1∶4)	69
3	L3	Ni(dme)Br₂	THF/DMA (4∶1)	24	13	L7	NiBr₂	THF/DMA (1∶4)	58
4	L4	Ni(dme)Br₂	THF/DMA (4∶1)	Trace	14	L7	NiCl₂	THF/DMA (1∶4)	52
5	L5	Ni(dme)Br₂	THF/DMA (4∶1)	40	15	L7	Ni(OTf)₂	THF/DMA (1∶4)	24
6	L6	Ni(dme)Br₂	THF/DMA (4∶1)	Trace	16	L7	Ni(acac)₂	THF/DMA (1∶4)	40
7	L7	Ni(dme)Br₂	THF/DMA (4∶1)	58	17^c	L7	Ni(dme)Br₂	THF/DMA (1∶4)	90
8	L7	Ni(dme)Br₂	THF	47	18^c^,^d	L7	Ni(dme)Br₂	THF/DMA (1∶4)	0
9	L7	Ni(dme)Br₂	DMA	34	19^c^,^e	L7	Ni(dme)Br₂	THF/DMA (1∶4)	81
10	L7	Ni(dme)Br₂	MeCN	23

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