Visible Light-Promoted, Photocatalyst-Free C(sp2)-H Bond Functionalization of Indolizines via EDA Complexes

被引：4
作者：
Mane, Kishor D. [1 ,2 ]
Rupanawar, Bapurao D. [1 ,2 ]
Suryavanshi, Gurunath [1 ,2 ]
机构：
[1] CSIR, Natl Chem Lab, Chem Engn & Proc Dev Div, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 2022卷 / 18期
关键词：
Blue LED; CDC; EDA; Indolizine; Quinone; PHOTOREDOX CATALYSIS; METAL; DERIVATIVES; ARYLATION; EFFICIENT; DRIVEN;
D O I：
10.1002/ejoc.202200261
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The catalyst and additive-free, photo-driven cross dehydrogenative coupling (CDC) reaction initiated by electron donor-acceptor (EDA) complexes between electron rich indolizines and electron poor quinones has been demonstrated. This green transformation reveals the advantages of operational simplicity, mild reaction conditions and good functional group tolerances.
引用
收藏
页数：8
相关论文
共 47 条
[1]   C-H Activation/Metalation Approaches for the Synthesis of Indolizine Derivatives [J].
Bertallo, Camila R. de S. ;
Arroio, Thais R. ;
Toledo, Monica F. Z. J. ;
Sadler, Scott A. ;
Vessecchi, Ricardo ;
Steel, Patrick G. ;
Clososki, Giuliano C. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (31-32) :5205-5213
[2]   Enantioselective radical conjugate additions driven by a photoactive intramolecular iminium-ion-based EDA complex [J].
Cao, Zhong-Yan ;
Ghosh, Tamal ;
Melchiorre, Paolo .
NATURE COMMUNICATIONS, 2018, 9
[3]   Non-imidazole heterocyclic histamine H3 receptor antagonists [J].
Chai, WY ;
Breitenbucher, JG ;
Kwok, A ;
Li, XB ;
Wong, V ;
Carruthers, NI ;
Lovenberg, TW ;
Mazur, C ;
Wilson, SJ ;
Axe, FU ;
Jones, TK .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (10) :1767-1770
[4]   Novel indolizine compounds as potent inhibitors of phosphodiesterase IV (PDE4): structure-activity relationship [J].
Chen, Shoujun ;
Xia, Zhiqiang ;
Nagai, Masazumi ;
Lu, Rongzhen ;
Kostik, Elena ;
Przewloka, Teresa ;
Song, Minghu ;
Chimmanamada, Dinesh ;
James, David ;
Zhang, Shijie ;
Jiang, Jun ;
Ono, Mitsunori ;
Koya, Keizo ;
Sun, Lijun .
MEDCHEMCOMM, 2011, 2 (03) :176-180
[5]   Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes [J].
Crisenza, Giacomo E. M. ;
Mazzarella, Daniele ;
Melchiorre, Paolo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (12) :5461-5476
[6]   Inhibitory activities of indolizine derivatives: a patent review [J].
Dawood, Kamal M. ;
Abbas, Ashraf A. .
EXPERT OPINION ON THERAPEUTIC PATENTS, 2020, 30 (09) :695-714
[7]  
Hu C., 2021, ORG LETT, V23, P3913
[8]  
Hui JR, 2021, ORG BIOMOL CHEM, V19, P10245, DOI [10.1039/d1ob01431e, 10.1039/D1OB01431E]
[9]   Photocatalyst-Free, Visible-Light-Mediated C(sp3)-H Arylation of Amides via a Solvent-Caged EDA Complex [J].
Kaur, Jaspreet ;
Shahin, Ahmed ;
Barham, Joshua P. .
ORGANIC LETTERS, 2021, 23 (06) :2002-2006
[10]   Discovery, Understanding, and Bioapplication of Organic Fluorophore: A Case Study with an Indolizine-Based Novel Fluorophore, Seoul-Fluor [J].
Kim, Eunha ;
Lee, Youngjun ;
Lee, Sanghee ;
Park, Seung Bum .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (03) :538-547
12345