Aromatization-Driven Cascade [1,5]-Hydride Transfer/Spirocyclization Promoted by Fluorinated Alcohols

被引：62

作者：

Lv, Xintong ^{[1
]}

Hu, Fangzhi ^{[1
]}

Duan, Kang ^{[1
]}

Li, Shuai-Shuai ^{[1
]}

Liu, Qing ^{[3
]}

Xiao, Jian ^{[1
,2
]}

机构：

[1] Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Peoples R China

[2] Qingdao Agr Univ, Coll Marine Sci & Engn, Qingdao 266109, Peoples R China

[3] Shandong Univ Sci & Technol, Coll Chem & Environm Engn, Qingdao 266590, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 04期

关键词：

PARA-QUINONE METHIDES; C-H FUNCTIONALIZATION; INTRAMOLECULAR HYDRIDE TRANSFER; C(SP(3))-H FUNCTIONALIZATION; BOND FUNCTIONALIZATION; EXPEDIENT SYNTHESIS; INDOLYL ALCOHOLS; DNA ALKYLATION; METAL-FREE; TRANSFER/CYCLIZATION;

D O I：

10.1021/acs.joc.8b02754

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aromatization-driven redox-neutral cascade [1,5]-hydride transfer/spirocyclization and cascade [1,5]-hydride transfer/hydrolysis from para-quinone methide in HFIP were developed. These protocols enabled the synthesis of azaspirocyclohexadienones and ortho-benzylated anilines in good to high yields under mild conditions, featuring room temperature, additive-free, and good functional group tolerance.

引用

页码：1833 / 1844

页数：12

共 95 条

[41] Synthesis of 3-Aryl-1-trifluoromethyltetrahydroisoquinolines by Bronsted Acid-Catalyzed C(sp3)-H Bond Functionalization [J].

Mori, Keiji ;

Umehara, Nobuaki ;

Akiyama, Takahiko .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (05) :901-906

[42] Selective Activation of Enantiotopic C(sp3)-Hydrogen by Means of Chiral Phosphoric Acid: Asymmetric Synthesis of Tetrahydroquinoline Derivatives [J].

Mori, Keiji ;

Ehara, Kensuke ;

Kurihara, Kazuki ;

Akiyama, Takahiko .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (16) :6166-6169

[43] Gold-Catalyzed Carbocyclization of Phenols with a Terminal Alkyne via an Intramolecular ipso-Friedel-Crafts Alkenylation [J].

Nemoto, Tetsuhiro ;

Matsuo, Nobuaki ;

Hamada, Yasumasa .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) :2417-2421

[44] Palladium-Catalyzed Intramolecular ipso-FriedelCrafts Alkylation of Phenols and Indoles: Rearomatization-Assisted Oxidative Addition [J].

Nemoto, Tetsuhiro ;

Zhao, Zengduo ;

Yokosaka, Takuya ;

Suzuki, Yuta ;

Wu, Riliga ;

Hamada, Yasumasa .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (08) :2217-2220

[45] Organocatalytic C-H activation reactions [J].

Pan, Subhas Chandra .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 :1374-1384

[46] para-Quinone Methide: a New Player in Asymmetric Catalysis [J].

Parra, Alejandro ;

Tortosa, Mariola .

CHEMCATCHEM, 2015, 7 (10) :1524-1526

[47] DNA alkylation properties of yatakemycin [J].

Parrish, JP ;

Kastrinsky, DB ;

Wolkenberg, SE ;

Igarashi, Y ;

Boger, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10971-10976

[48] Room temperature intramolecular hydro-O-alkylation of aldehydes:: sp3 C-H functionalization via a Lewis acid catalyzed tandem 1,5-hydride transfer/cyclization [J].

Pastine, SJ ;

Sames, D .

ORGANIC LETTERS, 2005, 7 (24) :5429-5431

[49] Room temperature hydroalkylation of electron-deficient olefins:: sp3 C-H functionalization via a Lewis acid-catalyzed intramolecular redox event [J].

Pastine, SJ ;

McQuaid, KM ;

Sames, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) :12180-12181

[50] The Redox-Neutral Approach to C-H Functionalization [J].

Peng, Bo ;

Maulide, Nuno .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (40) :13274-13287

← 1 2 3 4 5 6 7 8 9 10 →