Copper-Catalyzed Asymmetric Oxidative Cross-Coupling of 2-Naphthols with Aryl Methyl Ketones

被引：10

作者：

Deng, Tao ^{[1
]}

Wang, Hongjun ^{[1
]}

Cai, Chun ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Chem Engn Coll, Nanjing 210094, Jiangsu, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 07期

关键词：

Cross-coupling; Copper; Synthetic methods; Asymmetric catalysis; C-C coupling; H BOND FUNCTIONALIZATION; C-C; AEROBIC OXIDATION; ALPHA-KETOAMIDES; SYNTHETIC TOOLS; STRATEGY; 2-ACYLBENZOTHIAZOLES; BENZOTHIAZOLES; CONSTRUCTION; CYCLIZATION;

D O I：

10.1002/ejoc.201403512

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed asymmetric oxidative cross-coupling reaction of 2-naphthols with aryl methyl ketones has been developed. This transformation provides an efficient route to various functionalized naphtho[2,1-b]furan-1(2H)-ones in an enantiomerically enriched manner with molecular oxygen in air as the oxidant (52-89% yields, up to 87% ee). The reaction leads to the formation of a new quaternary carbon center within 3(2H)-furanones.

引用

页码：1569 / 1574

页数：6

共 69 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[2]

[Anonymous], 2013, Angew. Chem

[3]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]

[4] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[5] The current status and future trends in oxidation chemistry [J].

Beller, M .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) :107-108

[6] A Comparative Mechanistic Study of Cu-Catalyzed Oxidative Coupling Reactions with N-Phenyltetrahydroisoquinoline [J].

Boess, Esther ;

Schmitz, Corinna ;

Klussmann, Martin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (11) :5317-5325

[7] An organocatalytic oxidative coupling strategy for the direct synthesis of arylated quaternary stereogenic centers [J].

Bogle, Katherine M. ;

Hirst, David J. ;

Dixon, Darren J. .

ORGANIC LETTERS, 2007, 9 (23) :4901-4904

[8] Selective oxidative para C-C dimerization of 2,6-dimethylphenol [J].

Boldron, C ;

Aromí, G ;

Challa, G ;

Gamez, P ;

Reedijk, J .

CHEMICAL COMMUNICATIONS, 2005, (46) :5808-5810

[9] Gold-mediated C-H bond functionalisation [J].

Boorman, Tanya C. ;

Larrosa, Igor .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1910-1925

[10] A facile, metal- and solvent-free, autoxidative coupling of quinolines with indoles and pyrroles [J].

Brasse, Mikael ;

Ellman, Jonathan A. ;

Bergman, Robert G. .

CHEMICAL COMMUNICATIONS, 2011, 47 (17) :5019-5021

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