Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers

doi:10.6023/cjoc202211013

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (3): 1136-1145.DOI: 10.6023/cjoc202211013 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑；中国女科学家专辑

ARTICLES

苯基吩噻嗪多孔有机聚合物催化的非活化末端烯烃的卤代全氟烷基化反应

王睿^a, 高朗^a, 周岑^b, 张霄^a^,^*()

a 福建师范大学化学与材料学院福建省先进材料化工基础重点实验室福建省高分子材料重点实验室福州 350007
b 闽江学院材料与化学工程学院福建省中国漆新型材料工程研究中心福州 350108

收稿日期:2022-11-10 修回日期:2023-01-10 发布日期:2023-01-18
通讯作者: 张霄
作者简介:
† 共同第一作者.
基金资助:
国家自然科学基金(22071024); 国家自然科学基金(22271047); 福建省自然科学基金(2021J06020); 福建省自然科学基金(2022J011121); 闽江学院科研启动基金(MJY21027)

Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers

Rui Wang^a, Lang Gao^a, Cen Zhou^b, Xiao Zhang^a()

a Fujian Key Laboratory of Polymer Materials, Fujian Provincial Key Laboratory of Advanced Materials Oriented Chemical Engineering, College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350007
b Fujian Engineering and Research Center of New Chinese Lacquer Materials, College of Materials and Chemical Engineering, Minjiang University, Fuzhou 350108

Received:2022-11-10 Revised:2023-01-10 Published:2023-01-18
Contact: Xiao Zhang
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22071024); National Natural Science Foundation of China(22271047); Natural Science Foundation of Fujian Province(2021J06020); Natural Science Foundation of Fujian Province(2022J011121); Science and Technology Project of Minjiang University(MJY21027)

Photocatalytic heterogeneous chlorotrifluoromethylation and iodoperfluoroalkylation of unactivated terminal alkenes have been achieved under the catalysis of phenylphenothiazine-based porous organic polymer (PTH-POP). This method offers a transition-metal-free and recyclable platform to access valuable perfluoroalkylated compounds in a highly efficient fashion.

Key words: chlorotrifluoromethylation, heterogeneous, porous organic polymer, recyclability, transition-metal-free

Cite this article

Rui Wang, Lang Gao, Cen Zhou, Xiao Zhang. Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1136-1145.

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Entry	Catalyst	Base	Solvent	Yield^b/% of 3a
1	PTH-POP1	K₂HPO₄	CH₃CN	96 (88)^c
2	PTH-POP2	K₂HPO₄	CH₃CN	95
3	PTH-POP1	Na₂HPO₄	CH₃CN	94
4	PTH-POP1	NaHCO₃	CH₃CN	57
5	PTH-POP1	Et₃N	CH₃CN	47
6	PTH-POP1	DBU	CH₃CN	22
7	PTH-POP1	—	CH₃CN	89
8	PTH-POP1	K₂HPO₄	DMF	37
9	PTH-POP1	K₂HPO₄	Acetone	79
10	PTH-POP1	K₂HPO₄	THF	39
11	PTH-POP1	K₂HPO₄	DCE	94
12^d	—	K₂HPO₄	CH₃CN	0
13^e	PTH-POP1	K₂HPO₄	CH₃CN	0

Entry	Catalyst	Base	Solvent	Yield^b/% of 3a
1	PTH-POP1	K₂HPO₄	CH₃CN	96 (88)^c
2	PTH-POP2	K₂HPO₄	CH₃CN	95
3	PTH-POP1	Na₂HPO₄	CH₃CN	94
4	PTH-POP1	NaHCO₃	CH₃CN	57
5	PTH-POP1	Et₃N	CH₃CN	47
6	PTH-POP1	DBU	CH₃CN	22
7	PTH-POP1	—	CH₃CN	89
8	PTH-POP1	K₂HPO₄	DMF	37
9	PTH-POP1	K₂HPO₄	Acetone	79
10	PTH-POP1	K₂HPO₄	THF	39
11	PTH-POP1	K₂HPO₄	DCE	94
12^d	—	K₂HPO₄	CH₃CN	0
13^e	PTH-POP1	K₂HPO₄	CH₃CN	0

Entry	Catalyst	Reductant	Solvent	Yield^b/% of 5a
1	PTH-POP1	Sodium ascorbate	CH₃CN/CH₃OH	99 (86)^c
2	PTH-POP2	Sodium ascorbate	CH₃CN/CH₃OH	97
3	PTH-POP1	DIPEA	CH₃CN/CH₃OH	79
4	PTH-POP1	Et₃N	CH₃CN/CH₃OH	96
5^d	PTH-POP1	—	CH₃CN/CH₃OH	5
6^e	—	Sodium ascorbate	CH₃CN/CH₃OH	2
7^f	PTH-POP1	Sodium ascorbate	CH₃CN/CH₃OH	0

Entry	Catalyst	Reductant	Solvent	Yield^b/% of 5a
1	PTH-POP1	Sodium ascorbate	CH₃CN/CH₃OH	99 (86)^c
2	PTH-POP2	Sodium ascorbate	CH₃CN/CH₃OH	97
3	PTH-POP1	DIPEA	CH₃CN/CH₃OH	79
4	PTH-POP1	Et₃N	CH₃CN/CH₃OH	96
5^d	PTH-POP1	—	CH₃CN/CH₃OH	5
6^e	—	Sodium ascorbate	CH₃CN/CH₃OH	2
7^f	PTH-POP1	Sodium ascorbate	CH₃CN/CH₃OH	0

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苯基吩噻嗪多孔有机聚合物催化的非活化末端烯烃的卤代全氟烷基化反应

Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers

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