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
[51]   Retro-Diels-Alder reaction of 4H-1,2-benzoxazines to generate o-quinone methides:: Involvement of highly polarized transition states [J].
Sugimoto, Hiromichi ;
Nakamura, Satoshi ;
Ohwada, Tomohiko .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (26) :10088-10095
[52]   Phosphoric Acid Catalyzed [4+1]-Cycloannulation Reaction of ortho-Quinone Methides and Diazoketones: Catalytic, Enantioselective Access toward cis-2,3-Dihydrobenzofurans [J].
Suneja, Arun ;
Schneider, Christoph .
ORGANIC LETTERS, 2018, 20 (23) :7576-7580
[53]   CF3 oxonium salts, O-(trifluoromethyl)dibenzofuranium salts:: In situ synthesis, properties, and application as a real CF3+ species Reagent [J].
Umemoto, Teruo ;
Adachi, Kenji ;
Ishihara, Sumi .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (18) :6905-6917
[54]   Powerful, Thermally Stable, One-Pot-Preparable, and Recyclable Electrophilic Trifluoromethylating Agents: 2,8-Difluoro- and 2,3,7,8-Tetrafluoro-S-(trifluoromethyl)dibenzothiophenium Salts [J].
Umemoto, Teruo ;
Zhang, Bin ;
Zhu, Tianhao ;
Zhou, Xiaocong ;
Zhang, Peng ;
Hu, Song ;
Li, Yuanqiang .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (15) :7708-7719
[55]   o-quinone methides:: intermediates underdeveloped and underutilized in organic synthesis [J].
Van de Water, RW ;
Pettus, TRR .
TETRAHEDRON, 2002, 58 (27) :5367-5405
[56]  
Wang ZB, 2015, SYNTHESIS-STUTTGART, V47, P3629, DOI 10.1055/s-0035-1560356
[57]   Photocatalytic Radical Trifluoromethylation/Cyclization Cascade: Synthesis of CF3-Containing Pyrazolines and Isoxazolines [J].
Wei, Qiang ;
Chen, Jia-Rong ;
Hu, Xiao-Qiang ;
Yang, Xiao-Chen ;
Lu, Bin ;
Xiao, Wen-Jing .
ORGANIC LETTERS, 2015, 17 (18) :4464-4467
[58]   ortho-Quinone Methides in Natural Product Synthesis [J].
Willis, Nicky J. ;
Bray, Christopher D. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (30) :9160-9173
[59]   Regioselective α-Addition of Deconjugated Butenolides: Enantioselective Synthesis of Dihydrocoumarins [J].
Wu, Bo ;
Yu, Zhaoyuan ;
Gao, Xiang ;
Lan, Yu ;
Zhou, Yong-Gui .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (14) :4006-4010
[60]   C-H Oxidation/Michael Addition/Cyclization Cascade for Enantioselective Synthesis of Functionalized 2-Amino-4H-chromenes [J].
Wu, Bo ;
Gao, Xiang ;
Yan, Zhong ;
Chen, Mu-Wang ;
Zhou, Yong-Gui .
ORGANIC LETTERS, 2015, 17 (24) :6134-6137