Programmed Selective sp2 C-O Bond Activation toward Multiarylated Benzenes

被引：56

作者：

Zhao, Fei ^{[1
,2
]}

Zhang, Yun-Fei ^{[4
]}

Wen, Jing ^{[5
]}

Yu, Da-Gang ^{[1
,2
]}

Wei, Jiang-Bo ^{[1
,2
]}

Xi, Zhenfeng ^{[1
,2
,3
]}

Shi, Zhang-Jie ^{[1
,2
,3
]}

机构：

[1] Peking Univ, Coll Chem, Minist Educ, BNLMS, Beijing 100871, Peoples R China

[2] Peking Univ, Coll Chem, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

[3] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[4] China Agr Univ, Dept Chem, Beijing 100094, Peoples R China

[5] Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 13期

关键词：

CROSS-COUPLING REACTIONS; CARBON-CARBON BONDS; SUZUKI-MIYAURA; GRIGNARD-REAGENTS; STEREOCONTROLLED SYNTHESIS; BIOLOGICAL EVALUATION; BIARYL CONSTRUCTION; EFFICIENT SYNTHESIS; SYNTHETIC METHODS; DIRECT ARYLATION;

D O I：

10.1021/ol4011757

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of important multiarylated benzenes were efficiently synthesized from phloroglucinol derivatives 1 through sequential cross-couplings via Pd-catalyzed C-OTs, Ni-catalyzed C-OC(O)NEt2, and C-OMe bond activation. High selectivity was achieved based on the rational design and inherent diversity in the reactivity of different C-O bonds.

引用

页码：3230 / 3233

页数：4

共 101 条

[11] Nickel-catalyzed cross-coupling of aryl Grignard reagents with aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls [J].

Dankwardt, JW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) :2428-2432

[12] Synthesis of some new 1,3,4-thiadiazol-2-ylmethyl-1,2,4-triazole derivatives and investigation of their antimicrobial activities [J].

Demirbas, Ahmet ;

Sahin, Deniz ;

Demirbas, Neslihan ;

Karaoglu, Senguel Alpay .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (07) :2896-2903

[13] Stereocontrolled synthesis of tetrasubstituted olefins [J].

Flynn, Alison B. ;

Ogilvie, William W. .

CHEMICAL REVIEWS, 2007, 107 (11) :4698-4745

[14] A Modular and Scalable One-Pot Synthesis of Polysubstituted Furans [J].

Fournier, Jeremy ;

Arseniyadis, Stellios ;

Cossy, Janine .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (30) :7562-7566

[15] TOTAL SYNTHESIS OF ISOINDOLOBENZAZEPINE ALKALOIDS, LENNOXAMINE AND CHILENINE, BASED ON PALLADIUM-CATALYZED REDUCTION OF ALKENYL PHOSPHATES [J].

Fuwa, Haruhiko ;

Sasaki, Makoto .

HETEROCYCLES, 2008, 76 (01) :521-539

[16] A Ligand Free and Room Temperature Protocol for Pd-Catalyzed Kumada-Corriu Couplings of Unactivated Alkenyl Phosphates [J].

Gauthier, Delphine ;

Beckendorf, Stephan ;

Gogsig, Thomas M. ;

Lindhardt, Anders T. ;

Skrydstrup, Troels .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09) :3536-3539

[17] Synthesis and characterization of perfluoroaryl-substituted siloles and thiophenes: A series of electron-deficient blue light emitting materials [J].

Geramita, Katharine ;

McBee, Jennifer ;

Shen, Yulong ;

Radu, Nora ;

Tilley, T. Don .

CHEMISTRY OF MATERIALS, 2006, 18 (14) :3261-3269

[18] C(aryl)-O Activation of Aryl Carboxylates in Nickel-Catalyzed Biaryl Syntheses [J].

Goossen, Lukas J. ;

Goossen, Kaethe ;

Stanciu, Corneliu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (20) :3569-3571

[19] Biaryl Construction via Ni-Catalyzed C-O Activation of Phenolic Carboxylates [J].

Guan, Bing-Tao ;

Wang, Yang ;

Li, Bi-Jie ;

Yu, Da-Gang ;

Shi, Zhang-Jie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) :14468-+

[20] Methylation of arenes via Ni-catalyzed aryl C-O/F activation [J].

Guan, Bing-Tao ;

Xiang, Shi-Kai ;

Wu, Tao ;

Sun, Zuo-Peng ;

Wang, Bi-Qin ;

Zhao, Ke-Qing ;

Shi, Zhang-Jie .

CHEMICAL COMMUNICATIONS, 2008, (12) :1437-1439

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