Visible-Light-Driven Base-Promoted Radical Cascade Difluoroalkylation-Cyclization-Iodination of 1,6-Enynes with Ethyl Difluoroiodoacetate

被引：8

作者：

Wang, Yan ^{[1
]}

Liu, Ruyan ^{[1
]}

Zhou, Pengsheng ^{[1
]}

Wu, Jianglong ^{[1
]}

Li, Wenshuang ^{[1
]}

Wang, Chenyu ^{[1
]}

Li, Hao ^{[1
]}

Li, Dianjun ^{[1
,2
]}

Yang, Jinhui ^{[1
,2
]}

机构：

[1] Ningxia Univ, Sch Chem & Chem Engn, 489 Helanshan West Rd, Yinchuan, Ningxia, Peoples R China

[2] Ningxia Univ, State Key Lab High Efficiency Utilizat Coal & Gre, 489 Helanshan West Rd, Yinchuan, Ningxia, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 2022卷 / 05期

基金：

中国国家自然科学基金;

关键词：

Base-promoted; Cyclization; Difluoroalkylation; Radical reactions; Visible-light-driven; ELECTRON-TRANSFER; FLUORINE; METALLAPHOTOREDOX; ALKYLATION; ARYLATION;

D O I：

10.1002/ejoc.202101395

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A visible-light-driven base-promoted radical cascade difluoroalkylation/5-exo-dig cyclization/iodination of 1,6-enynes with ethyl difluoroiodoacetate was developed under catalyst-free and oxidant-free conditions. The difluoroalkylated pyrrolidines and tetrahydrofuran derivatives were generated with good functional group tolerance and high Z/E stereoselectivity. This reaction provided an alternative and mild method for the preparation of highly functionalized and vinyl C-I bonds containing five-membered heterocyclic products.

引用

页数：4

共 70 条

[41] Good Partnership between Sulfur and Fluorine: Sulfur-Based Fluorination and Fluoroalkylation Reagents for Organic Synthesis
Ni, Chuanfa
Hu, Mingyou
Hu, Jinbo
[J]. CHEMICAL REVIEWS, 2015, 115 (02) : 765 - 825
[42] 3D global aromaticity in a fully conjugated diradicaloid cage at different oxidation states
Ni, Yong
Gopalakrishna, Tullimilli Y.
Phan, Hoa
Kim, Taeyeon
Herng, Tun Seng
Han, Yi
Tao, Tao
Ding, Jun
Kim, Dongho
Wu, Jishan
[J]. NATURE CHEMISTRY, 2020, 12 (03) : 242 - +
[43] Influence of the difluoromethylene group (CF2) on the conformation and properties of selected organic compounds
O'Hagan, David
Wang, Yi
Skibinski, Maciej
Slawin, Alexandra M. Z.
[J]. PURE AND APPLIED CHEMISTRY, 2012, 84 (07) : 1587 - 1595
[44] Tri- and di-fluoroethylation of alkenes by visible light photoredox catalysis
Pan, Xiao-Yang
Zhao, Yue
Qu, Hong-An
Lin, Jin-Hong
Hang, Xiao-Chun
Xiao, Ji-Chang
[J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (09): : 1452 - 1456
[45] Metallaphotoredox aryl and alkyl radiomethylation for PET ligand discovery
Pipal, Robert W.
Stout, Kenneth T.
Musacchio, Patricia Z.
Ren, Sumei
Graham, Thomas J. A.
Verhoog, Stefan
Gantert, Liza
Lohith, Talakad G.
Schmitz, Alexander
Lee, Hsiaoju S.
Hesk, David
Hostetler, Eric D.
Davies, Ian W.
MacMillan, David W. C.
[J]. NATURE, 2021, 589 (7843) : 542 - +
[46] Selective fluoroalkylations with fluorinated sulfones, sulfoxides, and Sulfides
Prakash, G. K. Surya
Hu, Jinbo
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (10) : 921 - 930
[47] Fluorine in medicinal chemistry
Purser, Sophie
Moore, Peter R.
Swallow, Steve
Gouverneur, Veronique
[J]. CHEMICAL SOCIETY REVIEWS, 2008, 37 (02) : 320 - 330
[48] Visible-Light-Driven Photoredox-Catalyzed Three-Component Radical Cyanoalkylfluorination of Alkenes with Oxime Esters and a Fluoride Ion
Qian, Hao
Chen, Jun
Zhang, Bin
Cheng, Ying
Xiao, Wen-Jing
Chen, Jia-Rong
[J]. ORGANIC LETTERS, 2021, 23 (17) : 6987 - 6992
[49] Synthesis of Trifluoromethylated and gem-Difluoromethylenated Biologically Interesting Compounds from Fluorine-Containing Synthons
Qing, Feng-Ling
Zheng, Feng
[J]. SYNLETT, 2011, (08) : 1052 - 1072
[50] The merger of decatungstate and copper catalysis to enable aliphatic C(sp3)-H trifluoromethylation
Sarver, Patrick J.
Bacauanu, Vlad
Schultz, Danielle M.
DiRocco, Daniel A.
Lam, Yu-hong
Sherer, Edward C.
MacMillan, David W. C.
[J]. NATURE CHEMISTRY, 2020, 12 (05) : 459 - +

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