Metal-free oxidative cross-dehydrogenative coupling of quinones with benzylic C(sp3)-H bonds

被引：16

作者：

Dong, Yu ^{[1
,2
]}

Yang, Jian ^{[1
,2
]}

He, Shuai ^{[3
]}

Shi, Zhi-Chuan ^{[3
]}

Wang, Yu ^{[4
]}

Zhang, Xiao-Mei ^{[1
]}

Wang, Ji-Yu ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Sichuan, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

[3] Southwest Minzu Univ, Chengdu 610041, Sichuan, Peoples R China

[4] Guizhou Educ Univ, Guiyang 550018, Guizhou, Peoples R China

来源：

RSC ADVANCES | 2019年 / 9卷 / 47期

关键词：

C-C BOND; ALPHA-ARYLATION; H BONDS; DERIVATIVES; ACTIVATION; STRATEGY; ETHERS; ARYL; CASCADE; 1,4-NAPHTHOQUINONES;

D O I：

10.1039/c9ra05678e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A metal-free cross-dehydrogenative coupling of quinones with toluene derivatives has been established. A series of quinones were subjected to reaction with toluene derivatives in the presence of di-tertbutyl peroxide (DTBP) for direct synthesis of benzylquinones. The method exhibits good functional group tolerance, and desired products were obtained in moderate to good yields. Meanwhile, a radical pathway was proposed to describe the cross-dehydrogenative coupling of quinones with toluene derivatives.

引用

页码：27588 / 27592

页数：5

共 80 条

[1] Tetrabutylammonium Iodide Catalyzed Epoxidation of Naphthoquinone Derivatives with tert -Butyl Hydroperoxide as an Oxidant [J].

Ai, Bai-Ru ;

Chen, Xu-Ling ;

Dong, Yu ;

Tang, Lei ;

Wang, Ji-Yu .

SYNTHESIS-STUTTGART, 2017, 49 (17) :4017-4024

[2] Synthesis and Biological Evaluation of Novel Olean-28, 13β-lactams as Potential Antiprostate Cancer Agents [J].

Ai, Yong ;

Hu, Yang ;

Kang, Fenghua ;

Lai, Yisheng ;

Jia, Yanju ;

Huang, Zhangjian ;

Peng, Sixun ;

Ji, Hui ;

Tian, Jide ;

Zhang, Yihua .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (11) :4506-4520

[3] 1,4-Naphthoquinones in H-Bond-Directed Trienamine-Mediated Strategies [J].

Albrecht, Lukasz ;

Gomez, Clarisa Villegas ;

Jacobsen, Christian Borch ;

Jorgensen, Karl Anker .

ORGANIC LETTERS, 2013, 15 (12) :3010-3013

[4] Organocatalytic asymmetric vinylogous addition to quinones -: formation of optically active α-aryl ketones [J].

Aleman, Jose ;

Jacobsen, Christian Borch ;

Frisch, Kim ;

Overgaard, Jacob ;

Jorgensen, Karl Anker .

CHEMICAL COMMUNICATIONS, 2008, (05) :632-634

[5] Asymmetric organocatalytic α-arylation of aldehydes [J].

Aleman, Jose ;

Cabrera, Silvia ;

Maerten, Eddy ;

Overgaard, Jacob ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5520-5523

[6] Organocatalytic highly enantioselective α-arylation of β-ketoesters [J].

Aleman, Jose ;

Richter, Bo ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5515-5519

[7] Antitumour quinones [J].

Asche, C .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2005, 5 (05) :449-467

[8] Synthesis and in vitro activities of ferrocenic aminohydroxynaphthoquinones against Toxoplasma gondii and Plasmodium falciparum [J].

Baramee, A ;

Coppin, A ;

Mortuaire, M ;

Pelinski, L ;

Tomavo, S ;

Brocard, J .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (05) :1294-1302

[9] Cross Dehydrogenative Coupling (CDC) Reactions of N,N-Disubstituted Formamides, Benzaldehydes and Cycloalkanes [J].

Batra, Aanchal ;

Singh, Paramjit ;

Singh, Kamal Nain .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (29) :4927-4947

[10] Dynamic resolution of 2-cyclohexylidene acetaldehydes through organocatalytic dienamine [4+2] cycloaddition [J].

Blom, Jakob ;

Johansen, Tore Kiilerich ;

Jensen, Frank ;

Jorgensen, Karl Anker .

CHEMICAL COMMUNICATIONS, 2016, 52 (44) :7153-7156

← 1 2 3 4 5 6 7 8 →