Photo-Induced 3-Alkylation of Coumarins with Alkyl Halides

被引：0

作者：

Yan, Cheng ^{[1
]}

Zhang, Wen-Jiao ^{[1
]}

Qiu, Liu-Yan ^{[1
]}

Wang, Rui ^{[1
]}

Cao, Weiguo ^{[1
]}

Zhang, Zhikun ^{[1
]}

Tang, Xiao-Jun ^{[1
]}

机构：

[1] Shanghai Univ, Dept Chem, 99 Shangda Rd, Shanghai 200444, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2025年 / 367卷 / 06期

关键词：

Photoredox; Alkylation; Alkyl halide; Coumarin; Alkyl Radical; LIGHT; DIFLUOROALKYLATION; CASCADE; AMINES; DYES;

D O I：

10.1002/adsc.202401579

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A method for the direct 3-alkylation of coumarins utilizing alkyl halides as the alkylating agents has been achieved. This versatile reaction is compatible with a range of alkyl halides, including activated alkyl bromides, perfluoroalkyl iodides, and unactivated alkyl iodides. We propose a mechanism involving photoinduced electron transfer between alkyl halides and coumarins in the first singlet excited (S1) state, which generates alkyl radicals essential for the 3-alkylation process.

引用

页数：7

共 58 条

[1] Coumarin Derivatives as Photoinitiators in Photo-Oxidation and Photo-Reduction Processes and a Kinetic Model for Simulations of the Associated Polymerization Profiles [J].

Abdallah, Mira ;

Hijazi, Akram ;

Lin, Jui-Teng ;

Graff, Bernadette ;

Dumur, Frederic ;

Lalevee, Jacques .

ACS APPLIED POLYMER MATERIALS, 2020, 2 (07) :2769-2780

[2] Coumarins and Coumarin-Related Compounds in Pharmacotherapy of Cancer [J].

Akkol, Esra Kupeli ;

Genc, Yasin ;

Karpuz, Busra ;

Sobarzo-Sanchez, Eduardo ;

Capasso, Raffaele .

CANCERS, 2020, 12 (07) :1-25

[3] Advances in Synthesis and Potentially Bioactive of Coumarin Derivatives [J].

Anamika ;

Utreja, Divya ;

Ekta ;

Jain, Nisha ;

Sharma, Shivali .

CURRENT ORGANIC CHEMISTRY, 2018, 22 (26) :2509-2536

[4]

Awasthi R. S., 1986, SYNTHESIS, V12, p1061 1062

[5] Green-Light Activatable, Water-Soluble Red-Shifted Coumarin Photocages [J].

Bojtar, Marton ;

Kormos, Attila ;

Kis-Petik, Katalin ;

Kellermayer, Miklos ;

Kele, Peter .

ORGANIC LETTERS, 2019, 21 (23) :9410-9414

[6] Coumarin-Based Small-Molecule Fluorescent Chemosensors [J].

Cao, Duxia ;

Liu, Zhiqiang ;

Verwilst, Peter ;

Koo, Seyoung ;

Jangjili, Paramesh ;

Kim, Jong Seung ;

Lin, Weiying .

CHEMICAL REVIEWS, 2019, 119 (18) :10403-10519

[7] Visible-Light-Induced Direct Csp2-H Radical Trifluoroethylation of Coumarins with 1,1,1-Trifluoro-2-iodoethane (CF3CH2I) [J].

Chen, Xiaoyu ;

Li, Linlin ;

Pei, Congcong ;

Li, Jingya ;

Zou, Dapeng ;

Wu, Yangjie ;

Wu, Yusheng .

JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (03) :2772-2783

[8] Photoinitiated Deaminative Alkylation of Quinoxalin-2(1H)-ones via Electron Catalysis [J].

Deng, Yangling ;

Cheng, Xiya ;

Tan, Heping ;

He, Yuxuan ;

Zhang, Changmei ;

Qiu, Guanyinsheng ;

Zheng, Danqing .

ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (06) :865-870

[9] A ONE-STEP GENERAL-SYNTHESIS OF 3-BENZYLCOUMARINS [J].

DESHMUKH, SY ;

KELKAR, SL ;

WADIA, MS .

SYNTHETIC COMMUNICATIONS, 1990, 20 (06) :855-863

[10] Cobalt-Catalyzed Twofold Direct C(sp2)-C(sp3) Bond Coupling: Regioselective C-3 Alkylation of Coumarins with (Cyclo)alkyl Ethers [J].

Dian, Longyang ;

Zhao, Hui ;

Zhang-Negrerie, Daisy ;

Du, Yunfei .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (15) :2422-2426

← 1 2 3 4 5 6 →