Regiodivergent C-H Arylation of Triphenylene Derivatives Controlled by Electronic Effects of Diaryliodonium Salts

被引：5

作者：

Zhao, Ke ^{[1
]}

Du, Yu ^{[1
]}

Peng, Qiong ^{[1
]}

Yu, Wen-Hao ^{[1
]}

Wang, Bi-Qin ^{[1
]}

Feng, Chun ^{[1
]}

Xiang, Shi-Kai ^{[1
]}

机构：

[1] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610068, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 03期

基金：

中国国家自然科学基金;

关键词：

SITE-SELECTIVE ARYLATION; BOND ARYLATION; CATALYST CONTROL; ACTIVATION; FUNCTIONALIZATION; REGIOSELECTIVITY; BORYLATION; INDOLES; ARENES; ALKYNYLATION;

D O I：

10.1021/acs.joc.0c02900

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regiodivergent C-H arylation of triphenylene derivatives with diaryliodonium salts was developed. The regiodivergence was controlled by electronic effects of diaryliodonium salts. When the aryl(mesityl)iodonium salts bearing strong electron-donating groups at the para-position of aryl groups were used, the arylation reactions occurred ortho to amide groups. However, if the aryl(mesityl)iodonium salts bearing electron-withdrawing groups or weak electron-donating groups at the paraposition of aryl groups were utilized, the arylation reactions occurred meta to amide groups.

引用

页码：2986 / 2997

页数：12

共 81 条

[1] Catalyst-Switchable Regiocontrol in the Direct Arylation of Remote CH Groups in Pyrazolo[1,5-a]pyrimidines [J].

Bedford, Robin B. ;

Durrant, Steven J. ;

Montgomery, Michelle .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (30) :8787-8790

[2] Enantioselective α-Arylation of N-Acyloxazolidinones with Copper(II)-bisoxazoline Catalysts and Diaryliodonium Salts [J].

Bigot, Aurelien ;

Williamson, Alice E. ;

Gaunt, Matthew J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (35) :13778-13781

[3] Catalyst-Controlled Regiodivergent C-H Arylation Site of Fluorinated 2-Arylpyridine Derivatives: Application to Luminescent Iridium(III) Complexes [J].

Boyaala, Rabab ;

Touzani, Rachid ;

Roisnel, Thierry ;

Dorcet, Vincent ;

Caytan, Elsa ;

Jacquemin, Denis ;

Boixel, Julien ;

Guerchais, Veronique ;

Doucet, Henri ;

Soule, Jean-Francois .

ACS CATALYSIS, 2019, 9 (02) :1320-1328

[4] N-Arylation of DABCO with Diaryliodonium Salts: General Synthesis of N-Aryl-DABCO Salts as Precursors for 1,4-Disubstituted Piperazines [J].

Bugaenko, Dmitry, I ;

Yurovskaya, Marina A. ;

Karchava, Alexander, V .

ORGANIC LETTERS, 2018, 20 (20) :6389-6393

[5] Site-selective Sp2 and benzylic Sp3 palladium-catalyzed direct arylation [J].

Campeau, Louis-Charles ;

Schipper, Derek J. ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3266-+

[6] Switching the Regioselectivity of Direct C-H Arylation of 1,3-Dimethyluracil [J].

Cernova, Miroslava ;

Pohl, Radek ;

Hocek, Michal .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (22) :3698-3701

[7] Mechanistic Understanding of the Unexpected Meta Selectivity in Copper-Catalyzed Anilide C-H Bond Arylation [J].

Chen, Bo ;

Hou, Xue-Long ;

Li, Yu-Xue ;

Wu, Yun-Dong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (20) :7668-7671

[8] Directing-Group-Free C7-Alkylations of N-Alkylindoles Mediated by Cationic Zirconium Complexes: Role of Bronsted Acid for Catalytic Manifold [J].

Chen, Ping ;

Hao, Yanhong ;

Wang, Xinxin ;

Yuan, Dan ;

Yao, Yingming ;

Ackermann, Lutz .

CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (30) :7292-7297

[9] RETRACTED: Site-selective enzymatic C-H amidation for synthesis of diverse lactams (Retracted article. See vol. 367, pg. 155, 2020) [J].

Cho, Inha ;

Jia, Zhi-Jun ;

Arnold, Frances H. .

SCIENCE, 2019, 364 (6440) :575-+

[10] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds [J].

Cho, JY ;

Tse, MK ;

Holmes, D ;

Maleczka, RE ;

Smith, MR .

SCIENCE, 2002, 295 (5553) :305-308

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