Modular Synthesis of Arylacetic Acid Esters, Thioesters, and Amides from Aryl Ethers via Rh(II)-Catalyzed Diazo Arylation

被引：15

作者：

Best, Daniel ^{[1
]}

Jean, Mickael ^{[1
]}

van de Weghe, Pierre ^{[1
]}

机构：

[1] Univ Rennes 1, UMR CNRS 6226, Inst Sci Chim Rennes, Equipe PNSCM,UFR Sci Biol & Pharmaceut, 2 Ave Prof Leon Bernard, F-35043 Rennes, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 17期

关键词：

CATALYZED ALPHA-ARYLATION; H BOND FUNCTIONALIZATION; BETA-KETO-ESTERS; ARYLBORONIC ACIDS; C(SP(2))-H BONDS; MELDRUMS ACID; COUPLING REACTIONS; CARBENE INSERTION; CARBOXYLIC-ACIDS; CROSS-COUPLINGS;

D O I：

10.1021/acs.joc.6b01426

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

One-pot formation of arylacetic acid esters, thioesters, and amides via Rh(II)-catalyzed arylation of a Meldrurn's acid-derived diazo reagent with electron-rich arenes is described. The methodology was used to efficiently synthesize an anticancer compound.

引用

收藏

页码：7760 / 7770

页数：11

相关论文

共 89 条

[1] Rhodium(III)- and Iridium(III)-Catalyzed C7 Alkylation of Indolines with Diazo Compounds [J].

Ai, Wen ;

Yang, Xueyan ;

Wu, Yunxiang ;

Wang, Xuan ;

Li, Yuanchao ;

Yang, Yaxi ;

Zhou, Bing .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) :17653-17657

[2] Diaryl ether derivatives as anticancer agents - a review [J].

Bedos-Belval, Florence ;

Rouch, Anne ;

Vanucci-Bacque, Corinne ;

Baltas, Michel .

MEDCHEMCOMM, 2012, 3 (11) :1356-1372

[3] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].

Bellina, Fabio ;

Rossi, Renzo .

CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146

[4] Direct Synthesis of 5-Aryl Barbituric Acids by Rhodium(II)-Catalyzed Reactions of Arenes with Diazo Compounds [J].

Best, Daniel ;

Burns, David J. ;

Lam, Hon Wai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (25) :7410-7413

[5] Iron-catalyzed C-O cross-couplings of phenols with aryl iodides [J].

Bistri, Olivia ;

Correa, Arkaitz ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :586-588

[6] Experimental and theoretical investigation of reversible interconversion, thermal reactions, and wavelength-dependent photochemistry of diazo Meldrum's acid and its diazirine isomer, 6,6-dimethyl-5,7-dioxa-1,2-diaza-spiro[2,5]oct-1-ene-4,8-dione [J].

Bogdanova, A ;

Popik, VV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (46) :14153-14162

[7] Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects [J].

Burgos, Carlos H. ;

Barder, Timothy E. ;

Huang, Xiaohua ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4321-4326

[8] Catalytic functionalization of low reactive C(sp3)-H and C(sp2)-H bonds of alkanes and arenes by carbene transfer from diazo compounds [J].

Caballero, Ana ;

Diaz-Requejo, M. Mar ;

Fructos, Manuel R. ;

Olmos, Andrea ;

Urbano, Juan ;

Perez, Pedro J. .

DALTON TRANSACTIONS, 2015, 44 (47) :20295-20307

[9] A counteranion triggered arylation strategy using diaryliodonium fluorides [J].

Chan, L. ;

McNally, A. ;

Toh, Q. Y. ;

Mendoza, A. ;

Gaunt, M. J. .

CHEMICAL SCIENCE, 2015, 6 (02) :1277-1281

[10] Formal C--H insertion of diketocarbene generated by rhodium(II)-catalyzed decomposition of diazodimedone into a benzene molecule [J].

Chapyshev, SV ;

Nakano, H ;

Ibata, T .

RUSSIAN CHEMICAL BULLETIN, 1996, 45 (02) :471-473

← 1 2 3 4 5 6 7 8 9 →