Palladium-Catalyzed Synthesis of Biaryl Ketones via tert-Butyl Isocyanide Insertion

被引：15

作者：

Chen, Zhong ^{[1
]}

Duan, Huaqing ^{[1
]}

Jiang, Xiao ^{[1
]}

Wang, Jinmei ^{[1
]}

Zhu, Yongming ^{[1
]}

Yang, Shilin ^{[1
]}

机构：

[1] Soochow Univ, Coll Pharmaceut Sci, Suzhou 215123, Peoples R China

来源：

SYNLETT | 2014年 / 25卷 / 10期

关键词：

isocyanide; carbonylative Suzuki coupling; palladium catalyst; diaryl ketone; insertion reaction; CROSS-COUPLING REACTION; ARYLBORONIC ACIDS; DIRECT ACCESS; ARYL HALIDES; DERIVATIVES; ALDEHYDES; ACTIVATION; INHIBITORS; 4-AMINOQUINAZOLINES; BENZOPHENONES;

D O I：

10.1055/s-0033-1341244

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient palladium-catalyzed carbonylative Suzuki coupling via tert-butyl isocyanide insertion has been developed, which demonstrates the utility of isocyanides in intermolecular C-C bond construction. This methodology provides a novel pathway for the synthesis of diaryl ketones in moderate to good yields. The approach is tolerant to a wide range of substrates and applicable to library synthesis. A possible reaction mechanism was proposed based on the experimental results.

引用

页码：1425 / 1430

页数：6

共 42 条

[11] Structure-Activity Relationships, Ligand Efficiency, and Lipophilic Efficiency Profiles of Benzophenone-Type Inhibitors of the Multidrug Transporter P-Glycoprotein [J].

Jabeen, Ishrat ;

Pleban, Karin ;

Rinner, Uwe ;

Chiba, Peter ;

Ecker, Gerhard F. .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (07) :3261-3273

[12] Synthesis of biarylketones and phthalides from organoboronic acids and aldehydes catalyzed by cobalt complexes [J].

Karthikeyan, Jaganathan ;

Parthasarathy, Kanniyappan ;

Cheng, Chien-Hong .

CHEMICAL COMMUNICATIONS, 2011, 47 (37) :10461-10463

[13] Potential cancer chemopreventive in vitro activities of monomeric xanthone derivatives from the marine algicolous fungus Monodictys putredinis [J].

Krick, Anja ;

Kehraus, Stefan ;

Gerhaeuser, Clarissa ;

Klimo, Karin ;

Nieger, Martin ;

Maier, Armin ;

Fiebig, Heinz-Herbert ;

Atodiresei, Iuliana ;

Raabe, Gerhard ;

Fleischhauer, Joerg ;

Koenig, Gabriele M. .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (03) :353-360

[14] Unravelling the labyrinth of palladium-catalysed reactions involving isocyanides [J].

Lang, Stuart .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) :4867-4880

[15] Identification of CKD-516: A Potent Tubulin Polymerization Inhibitor with Marked Antitumor Activity against Murine and Human Solid Tumors [J].

Lee, Jaekwang ;

Kim, Soo Jin ;

Choi, Hojin ;

Kim, Young Hoon ;

Lim, In Tack ;

Yang, Hyun-mo ;

Lee, Chang Sik ;

Kang, Hee Ryong ;

Ahn, Soon Kil ;

Moon, Seung Kee ;

Kim, Dal-Hyun ;

Lee, Sungsook ;

Choi, Nam Song ;

Lee, Kyung Joo .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (17) :6337-6354

[16] Palladium-Catalyzed C-C Coupling of Aryl Halides with Isocyanides: An Alternative Method for the Stereoselective Synthesis of (3E)-(Imino)isoindolin-1-ones and (3E)-(Imino)thiaisoindoline 1,1-Dioxides [J].

Liu, Bifu ;

Li, Yibiao ;

Jiang, Huanfeng ;

Yin, Meizhou ;

Huang, Huawen .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (11-12) :2288-2300

[17] Palladium-Catalyzed Denitrogenation Reaction of 1,2,3-Benzotriazin-4(3H)-ones Incorporating Isocyanides [J].

Miura, Tomoya ;

Nishida, Yui ;

Morimoto, Masao ;

Yamauchi, Motoshi ;

Murakami, Masahiro .

ORGANIC LETTERS, 2011, 13 (06) :1429-1431

[18] Palladium-Catalyzed Cascade Process Consisting of Isocyanide Insertion and Benzylic C(sp3)-H Activation: Concise Synthesis of Indole Derivatives [J].

Nanjo, Takeshi ;

Tsukano, Chihiro ;

Takemoto, Yoshiji .

ORGANIC LETTERS, 2012, 14 (16) :4270-4273

[19] Bicyclic Substituted Hydroxyphenylmethanones as Novel Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 1 (17β-HSD1) for the Treatment of Estrogen-Dependent Diseases [J].

Oster, Alexander ;

Hinsberger, Stefan ;

Werth, Ruth ;

Marchais-Oberwinkler, Sandrine ;

Frotscher, Martin ;

Hartmann, Rolf W. .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (22) :8176-8186

[20] DMC mediated one pot synthesis of biaryl ketones from aryl carboxylic and boronic acids [J].

Pathak, Arunendra ;

Rajput, Chatrasal S. ;

Bora, Pushkar S. ;

Sharma, Somesh .

TETRAHEDRON LETTERS, 2013, 54 (17) :2149-2150

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