Copper-Catalyzed Decarboxylative Cross-Coupling of α‑Fluoroacrylic Acids with N-Tosyl Oxaziridines

doi:10.6023/cjoc202208010

Abstract

A protocol for the copper-catalyzed decarboxylative cross-coupling of α‑fluoroacrylic acids with N-tosyl oxaziridines was reported. A series of substituted α-fluoroacrylic acids, and primary, secondary and tertiary substituted oxaziridines were suitable reaction substrates. The decarboxylation reaction exhibited good functional group compatibility and excellent Z-stereoselectivity. This method provides a novel and practical strategy for the construction of monofluoroalkenes, which are key functional groups in the pharmaceutical and material sciences. In addition to α-fluoroacrylic acids, β- fluoroacrylic acid could also participate in the reaction smoothly, which provides a protocol to access various substituted monofluoroalkenes. This methodology also provides a platform for the modification of complex biologically active molecules.

Key words: fluoroacrylic acids, oxaziridines, copper-catalyzed, monofluoroalkene, decarboxylative

Cite this article

Xiaoyu Lu, Xiaomei Sun, Yaqing Niu, Junchao Wang, Wenjing Yin, Mengting Gao, Zi Liu, Zhenghuan Wei, Tinghua Tao. Copper-Catalyzed Decarboxylative Cross-Coupling of α‑Fluoroacrylic Acids with N-Tosyl Oxaziridines[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2110-2119.

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Entry^a	Catalyst	Ligand	Solvent	Yield/% (Z:E>30:1)
1	CuI	L1	DCE	37
2	CuBr	L1	DCE	26
3	CuCl	L1	DCE	25
4	CuTc	L1	DCE	55
5	Cu₂O	L1	DCE	62
6	CuOTf^.Ph	L1	DCE	40
7	Cu(CH₃CN)₄PF₆	L1	DCE	78
8	Fe(OAc)₂	L1	DCE	35
9	Cu(OTf)₂	L1	DCE	42
10	Cu(acac)₂	L1	DCE	72
11	CuO	L1	DCE	28
12	CuBr₂	L1	DCE	29
13	Cu(OAc)₂	L1	DCE	31
14	Cu(CH₃CN)₄PF₆	L2	DCE	37
15	Cu(CH₃CN)₄PF₆	L3	DCE	22
16	Cu(CH₃CN)₄PF₆	L4	DCE	18
17	Cu(CH₃CN)₄PF₆	L1	PhF	45
18	Cu(CH₃CN)₄PF₆	L1	PhCl	56
19	Cu(CH₃CN)₄PF₆	L1	PhH	43
20	Cu(CH₃CN)₄PF₆	L1	PhH/DCE (V:V=1:1)	38
21	Cu(CH₃CN)₄PF₆	L1	DCE	69
22	Cu(CH₃CN)₄PF₆	L1	DCE	65
23	—	L1	DCE	Trace

Entry^a	Catalyst	Ligand	Solvent	Yield/% (Z:E>30:1)
1	CuI	L1	DCE	37
2	CuBr	L1	DCE	26
3	CuCl	L1	DCE	25
4	CuTc	L1	DCE	55
5	Cu₂O	L1	DCE	62
6	CuOTf^.Ph	L1	DCE	40
7	Cu(CH₃CN)₄PF₆	L1	DCE	78
8	Fe(OAc)₂	L1	DCE	35
9	Cu(OTf)₂	L1	DCE	42
10	Cu(acac)₂	L1	DCE	72
11	CuO	L1	DCE	28
12	CuBr₂	L1	DCE	29
13	Cu(OAc)₂	L1	DCE	31
14	Cu(CH₃CN)₄PF₆	L2	DCE	37
15	Cu(CH₃CN)₄PF₆	L3	DCE	22
16	Cu(CH₃CN)₄PF₆	L4	DCE	18
17	Cu(CH₃CN)₄PF₆	L1	PhF	45
18	Cu(CH₃CN)₄PF₆	L1	PhCl	56
19	Cu(CH₃CN)₄PF₆	L1	PhH	43
20	Cu(CH₃CN)₄PF₆	L1	PhH/DCE (V:V=1:1)	38
21	Cu(CH₃CN)₄PF₆	L1	DCE	69
22	Cu(CH₃CN)₄PF₆	L1	DCE	65
23	—	L1	DCE	Trace

铜催化氟代丙烯酸与氧杂吖丙啶的脱羧交叉偶联反应