CuCl2-Catalyzed α-Chloroketonation of Aromatic Alkenes via Visible-Light-Induced LMCT

被引：6

作者：

He, Xing-Xian ^{[1
]}

Chang, Huan-Huan ^{[1
]}

Zhao, Ying-Xue ^{[1
]}

Li, Xiang-Jie ^{[1
]}

Liu, Sheng-An ^{[1
]}

Zang, Zhong-Lin ^{[1
]}

Zhou, Cheng-He ^{[1
]}

Cai, Gui-Xin ^{[1
]}

机构：

[1] Southwest Univ, Inst Bioorgan & Med Chem, Sch Chem & Chem Engn, Key Lab Qual & Safety Control Citrus Fruits,Minis, Chongqing 400715, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2023年 / 18卷 / 01期

关键词：

aromatic alkenes; alpha-chloroketones; CuCl2; LMCT; photocatalysis; C-H BOND; N-BROMOSUCCINIMIDE; AMMONIUM-CHLORIDE; METAL-FREE; KETONES; CHLORINATION; MILD; BROMINATION; ALKYNES; REACTIVITY;

D O I：

10.1002/asia.202200954

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Here we report a copper-catalyzed protocol for the synthesis of alpha-chloroketones from aromatic alkenes including electron-deficient olefins under visible-light irradiation. Preliminary mechanistic studies show that the peroxo Cu(II) species is the key intermediate and hydroperoxyl (HOO.) and chlorine (Cl.) radicals can be generated by ligand-to-metal charge transfer (LMCT).

引用

页数：5

共 50 条

[1] Visible-Light-Induced Vicinal Dichlorination of Alkenes through LMCT Excitation of CuCl2
Lian, Pengcheng
Long, Wenhao
Li, Jingjing
Zheng, Yonggao
Wan, Xiaobing
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (52) : 23603 - 23608
[2] Visible-Light-Induced Acylation/Arylation of Alkenes via Aryl Migration/Desulfonylation
Luo, Zhen-Tao
Fan, Jian-Hong
Xiong, Bi-Quan
Liu, Yu
Tang, Ke-Wen
Huang, Peng-Fei
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (35)
[3] Visible-Light-Induced Arylthiofluoroalkylations of Unactivated Heteroaromatics and Alkenes
Choi, Yeojin
Yu, Chunghyeon
Kim, Jun Soo
Cho, Eun Jin
ORGANIC LETTERS, 2016, 18 (13) : 3246 - 3249
[4] Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids
Jiang, Min
Yang, Haijun
Jin, Yunhe
Ou, Lunyu
Fu, Hua
SYNLETT, 2018, 29 (12) : 1572 - 1577
[5] Visible light-enabled regioselective chlorination of coumarins using CuCl2via LMCT excitation
Li, Weiming
Liu, Jinshan
Zhou, Min
Ma, Lin
Zhang, Min
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (33) : 6667 - 6672
[6] Visible-Light-Induced Oxidative α-keto-Dichlorination of Arylalkynes by CuCl2 at Room Temperature
Charpe, Vaibhav Pramod
Gupta, Mahima
Hwang, Kuo Chu
CHEMSUSCHEM, 2022, 15 (17)
[7] Iron-Catalyzed Ipso-Nitration of Aryl Borides via Visible-Light-Induced β-Homolysis
Liu, Shuyang
Lu, Yusheng
Wang, Hongyao
Xue, Zhiyan
Xu, Ziyi
Wan, Huihui
Yin, Qingxin
Lv, Tianming
Liu, Shu-Xin
Jin, Yunhe
ACS CATALYSIS, 2025, 15 (04): : 3306 - 3313
[8] Visible-Light-Induced Acridinium-Catalyzed Acylation of Isoquinolines with Aldehydes via HAT
Singh, Satya Prakash
Singh, Praveen P.
Mishra, Mangla
Tivari, Shraddha
Singh, Pravin K.
Srivastava, Vishal
SYNLETT, 2025,
[9] Synthesis of Perfluorinated Isoquinolinediones through Visible-Light-Induced Cyclization of Alkenes
Tang, Shi
Deng, You-Lin
Li, Jie
Wang, Wen-Xin
Ding, Guo-Liang
Wang, Ming-Wei
Xiao, Zhu-Ping
Wang, Ying-Chun
Sheng, Rui-Long
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24) : 12599 - 12605
[10] Visible-light-induced Synthesis of Organic Peroxides via Decarboxylative Couplings of Carboxylic Acids, Alkenes and tert-Butyl Hydroperoxide
Huang, Qiuwei
Lou, Chenhao
Lv, Leiyang
Li, Zhiping
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2024, 40 (05) : 863 - 873

← 1 2 3 4 5 →