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

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 21期

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

页码：3117 / 3120

页数：4

共 70 条

[11] Formal [4+1] Annulation Reactions in the Synthesis of Carbocyclic and Heterocyclic Systems [J].

Chen, Jia-Rong ;

Hu, Xiao-Qiang ;

Lu, Liang-Qiu ;

Xiao, Wen-Jing .

CHEMICAL REVIEWS, 2015, 115 (11) :5301-5365

[12] A mild method for generation of o-quinone methides under basic conditions. The facile synthesis of trans-2,3-dihydrobenzofurans [J].

Chen, Mu-Wang ;

Cao, Liang-Liang ;

Ye, Zhi-Shi ;

Jiang, Guo-Fang ;

Zhou, Yong-Gui .

CHEMICAL COMMUNICATIONS, 2013, 49 (16) :1660-1662

[13] Enantioselective Reactions of 2-Sulfonylalkyl Phenols with Allenic Esters: Dynamic Kinetic Resolution and [4+2] Cycloaddition Involving ortho-Quinone Methide Intermediates [J].

Chen, Ping ;

Wang, Kai ;

Guo, Wengang ;

Liu, Xianghui ;

Liu, Yan ;

Li, Can .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (13) :3689-3693

[14] Photoactivation of amino-substituted 1,4-benzoquinones for release of carboxylate and phenolate leaving groups using visible light [J].

Chen, Yugang ;

Steinmetz, Mark G. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :6053-6060

[15] Asymmetric Cyclopropanation of β,γ-Unsaturated α-Ketoesters with Stabilized Sulfur Ylides Catalyzed by C2-Symmetric Ureas [J].

Cheng, Ying ;

An, Jing ;

Lu, Liang-Qiu ;

Luo, Lan ;

Wang, Zheng-Yi ;

Chen, Jia-Rong ;

Xiao, Wen-Jing .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01) :281-284

[16] Flash photolytic generation of ortho-quinone methide in aqueous solution and study of its chemistry in that medium [J].

Chiang, Y ;

Kresge, AJ ;

Zhu, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (33) :8089-8094

[17] Visible-light-induced photocatalytic oxytrifluoromethylation of N-allylamides for the synthesis of CF3-containing oxazolines and benzoxazines [J].

Deng, Qiao-Hui ;

Chen, Jia-Rong ;

Wei, Qiang ;

Zhao, Quan-Qing ;

Lu, Liang-Qiu ;

Xiao, Wen-Jing .

CHEMICAL COMMUNICATIONS, 2015, 51 (17) :3537-3540

[18] Bronsted Acid Catalyzed, Conjugate Addition of β-Dicarbonyls to In Situ Generated ortho-Quinone Methides-Enantioselective Synthesis of 4-Aryl-4H-Chromenes [J].

El-Sepelgy, Osama ;

Haseloff, Stefan ;

Alamsetti, Santosh Kumar ;

Schneider, Christoph .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (30) :7923-7927

[19] Unified Total Syntheses of (-)-Medicarpin, (-)-Sophoracarpan A, and (±)-Kushecarpin A with Some Structural Revisions [J].

Feng, Zhen-Gao ;

Bai, Wen-Ju ;

Pettus, Thomas R. R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (06) :1864-1867

[20] Photoaddition of water and alcohols to the anthracene moiety of 9-(2′-hydroxyphenyl)anthracene via formal excited state intramolecular proton transfer [J].

Flegel, M ;

Lukeman, M ;

Huck, L ;

Wan, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (25) :7890-7897

← 1 2 3 4 5 6 7 →