Copper/Selectfluor Co-catalyzed Ritter-Type Benzylic C—H Amination

doi:10.6023/cjoc202409010

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (6): 2181-2188.DOI: 10.6023/cjoc202409010 Previous Articles Next Articles

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铜/Selectfluor共催化的苄基碳氢键Ritter胺基化反应

钱纯节^a^,^b^,^†, 何博洋^b^,^†, 刘兴宇^b, 王平^a, 高广春^b^,^*(), 刘石惠^b^,^*()

^a 浙江工业大学药学院杭州 310014
^b 嘉兴大学医学院浙江嘉兴 314001

收稿日期:2024-09-10 修回日期:2024-12-02 发布日期:2025-01-03
通讯作者: 高广春, 刘石惠
作者简介:
^†共同第一作者.
基金资助:
国家自然科学基金(22001096); 浙江省自然科学基金(LQ21B020008); 嘉兴市科技计划专项(2023AY40031); 嘉兴大学勤慎青年学者(CD70623026); 嘉兴大学“百青”培养人才(CD70621018)

Copper/Selectfluor Co-catalyzed Ritter-Type Benzylic C—H Amination

Chunjie Qian^a^,^b^,^†, Boyang He^b^,^†, Xingyu Liu^b, Ping Wang^a, Guangchun Gao^b^,^*(), Shihui Liu^b^,^*()

^a College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014
^b College of Medicine, Jiaxing University, Jiaxing, Zhejiang 314001

Received:2024-09-10 Revised:2024-12-02 Published:2025-01-03
Contact: Guangchun Gao, Shihui Liu
About author:
^†The authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22001096); Natural Science Foundation of Zhejiang Province(LQ21B020008); Project of Jiaxing Science and Technology Plan-Special Project for Young Scientific and Technological Talents(2023AY40031); Qin Shen Scholar Program of Jiaxing University(CD70623026); Jiaxing University “Hundred Youth” Training Talents(CD70621018)

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Chunjie Qian, Boyang He, Xingyu Liu, Ping Wang, Guangchun Gao, Shihui Liu. Copper/Selectfluor Co-catalyzed Ritter-Type Benzylic C—H Amination[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 2181-2188.

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Fig. & Tab. 4

References 20

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铜/Selectfluor共催化的苄基碳氢键Ritter胺基化反应

Copper/Selectfluor Co-catalyzed Ritter-Type Benzylic C—H Amination

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Entry	Photocatalyst	Oxidant	Metal	Ligand	Yield^b/%
1	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	Cu(OAc)₂	2,9-Me₂-1,10-phen	23
2	—	Selectfluor	Cu(OAc)₂	2,9-Me₂-1,10-phen	22
3^c	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	Cu(OAc)₂	2,9-Me₂-1,10-phen	24
4	[Ir{dF(CF₃)ppy}₂(dtbbpy)]PF₆	Selectfluor	Cu(OAc)₂	—	23
5^c	—	Selectfluor	Cu(OAc)₂	bpy	20
6^c^,^d	—	Selectfluor	Cu(OAc)₂	PPBO	16
7^c	—	Selectfluor	Cu(OAc)₂	—	23
8^c	—	Selectfluor	CuCl₂	—	43
9^c	—	Selectfluor	CuBr₂	—	29
10^c	—	Selectfluor	Cu(CF₃COO)₂•H₂O	—	31
11^c	—	Selectfluor	Cu(OTf)₂	—	27
12^c	—	Selectfluor	CuCl	—	37
13^c	—	Selectfluor	CuBr	—	39
14^c	—	Selectfluor	FeCl₃	—	n.d.^e
15^c^,^f	—	Selectfluor	CuCl₂	—	44
16^c^,^g	—	Selectfluor	CuCl₂	—	53
17^c^,^g	—	NFSI	CuCl₂	—	44
18^c^,^g	—	APS	CuCl₂	—	n.d.^e
19^c^,^h	—	Selectfluor	CuCl₂	—	35
20^c^,ⁱ	—	Selectfluor	CuCl₂	—	Trace
21^c^,^j	—	Selectfluor	CuCl₂	—	63
22^c^,^j	—	—	CuCl₂	—	n.d.^e
23^c^,^j	—	Selectfluor	—	—	n.d.^e

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(a) Alkylarene substrates 1a~1w

(b) Nitrile substrates 2b~2f

(a) Alkylarene substrates 1a~1w

(b) Nitrile substrates 2b~2f