A visible light photoredox catalyzed carbon radical-mediated generation of ortho-quinone methides for 2,3-dihydrobenzofuran synthesis

被引:55
作者
Zhou, Fan [1 ]
Cheng, Ying [1 ]
Liu, Xiao-Peng [1 ]
Chen, Jia-Rong [1 ]
Xiao, Wen-Jing [1 ,2 ]
机构
[1] Cent China Normal Univ, Int Joint Res Ctr Intelligent Biosensing Technol, Coll Chem, Key Lab Pesticide & Chem Biol,Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China
[2] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
关键词
DIELS-ALDER REACTIONS; ENANTIOSELECTIVE SYNTHESIS; BIOMIMETIC SYNTHESES; BETA-DICARBONYLS; FACILE SYNTHESIS; SULFUR YLIDES; ANNULATION; STRATEGY; REACTIVITY; COMPLEXES;
D O I
10.1039/c9cc00727j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A visible light photoredox-catalyzed carbon radical-mediated strategy for in situ formation of ortho-quinone methides from 2-vinyl phenols is described. This strategy enables a multicomponent cyclization reaction of 2-vinyl phenols, Umemoto's reagent, and sulfur ylides, providing access to trifluoromethylated 2,3-dihydrobenzofurans.
引用
收藏
页码:3117 / 3120
页数:4
相关论文
共 70 条
[1]   Applications of ortho-Quinone Methides in the Synthesis of Natural Products [J].
Ai, Wenying ;
Liao, Daohong ;
Lei, Xiaoguang .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (08) :1615-1626
[2]   Taming reactive phenol tautomers and o-quinone methides with transition metals:: A structure-reactivity relationship [J].
Amouri, H ;
Le Bras, J .
ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (07) :501-510
[3]   Dual Reactivity of Hydroxy- and Methoxy- Substituted o-Quinone Methides in Aqueous Solutions: Hydration versus Tautomerization [J].
Arumugam, Selvanathan ;
Popik, Vladimir V. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21) :7338-7346
[4]   The Domestication of ortho-Quinone Methides [J].
Bai, Wen-Ju ;
David, Jonathan G. ;
Feng, Zhen-Gao ;
Weaver, Marisa G. ;
Wu, Kun-Liang ;
Pettus, Thomas R. R. .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (12) :3655-3664
[5]   Mannich base-connected syntheses mediated by ortho-quinone methides [J].
Barta, Petra ;
Fulop, Ferenc ;
Szatmari, Istvan .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 :560-575
[6]   Generation of ortho-Quinone Methides by p-TsOH on Silica and Their Hetero-Diels-Alder Reactions with Styrenes [J].
Batsomboon, Paratchata ;
Phakhodee, Wong ;
Ruchirawat, Somsak ;
Ploypradith, Poonsakdi .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) :4009-4012
[7]   The Emergence of Quinone Methides in Asymmetric Organocatalysis [J].
Caruana, Lorenzo ;
Fochi, Mariafrancesca ;
Bernardi, Luca .
MOLECULES, 2015, 20 (07) :11733-11764
[8]   Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents [J].
Charpentier, Julie ;
Frueh, Natalja ;
Togni, Antonio .
CHEMICAL REVIEWS, 2015, 115 (02) :650-682
[9]   Photocascade Catalysis: A New Strategy for Cascade Reactions [J].
Chen, Jia-Rong ;
Yan, Dong-Mei ;
Wei, Qiang ;
Xiao, Wen-Jing .
CHEMPHOTOCHEM, 2017, 1 (05) :148-158
[10]   Exploration of Visible-Light Photocatalysis in Heterocycle Synthesis and Functionalization: Reaction Design and Beyond [J].
Chen, Jia-Rong ;
Hu, Xiao-Qiang ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) :1911-1923