Palladium-Catalyzed Regioselective C-H Acylation of Biaryl-2-amines

被引：17

作者：

Cai, Zhong-Jian ^{[1
]}

Yang, Chao ^{[1
]}

Wang, Shun-Yi ^{[1
]}

Ji, Shun-Jun ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 16期

基金：

中国国家自然科学基金;

关键词：

DECARBOXYLATIVE ORTHO ACYLATION; ALPHA-OXOCARBOXYLIC ACIDS; TERT-BUTYL HYDROPEROXIDE; BOND ACTIVATION; CARBON-MONOXIDE; DIRECTING GROUP; FREE-AMINE; ORTHO-ARYLATION; ALKENYLATION; DERIVATIVES;

D O I：

10.1021/acs.joc.5b00962

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed efficient C-H acylation reaction of biaryl-2-amines and aromatic aldehydes is developed. This dehydrogenative cross-coupling protocol could furnish monoacylation and diacylation products in moderate to good yields with a broad substrate scope and good regioselectivity.

引用

页码：7928 / 7936

页数：9

共 92 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Direct Alkylations of Ketimines [J].

Ackermann, Lutz ;

Hofmann, Nora ;

Vicente, Ruben .

ORGANIC LETTERS, 2011, 13 (07) :1875-1877

[2] Reactivity of cyclopalladated compounds derived from biphenyl-2-ylamine towards carbon monoxide, tbutyl isocyanide and alkynes [J].

Albert, Joan ;

D'Andrea, Lucia ;

Granell, Jaume ;

Zafrilla, Javier ;

Font-Bardia, Merce ;

Solans, Xavier .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (22) :4895-4902

[3] C-H Bond Activation in Transition Metal Species from a Computational Perspective [J].

Balcells, David ;

Clot, Eric ;

Eisenstein, Odile .

CHEMICAL REVIEWS, 2010, 110 (02) :749-823

[4] Palladium-Catalyzed Oxidative sp2 C-H Bond Acylation with Aldehydes [J].

Basle, Olivier ;

Bidange, Johan ;

Shuai, Qi ;

Li, Chao-Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (07) :1145-1149

[5] 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

[6] RhIII-Catalyzed Oxidative Olefination of Vinylic C-H Bonds: Efficient and Selective Access to Di-unsaturated α-Amino Acid Derivatives and Other Linear 1,3-Butadienes [J].

Besset, Tatiana ;

Kuhl, Nadine ;

Patureau, Frederic W. ;

Glorius, Frank .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (26) :7167-7171

[7] Palladium(II)-Catalyzed Direct ortho-C-H Acylation of Anilides by Oxidative Cross-Coupling with Aldehydes using tert-Butyl Hydroperoxide as Oxidant [J].

Chan, Chun-Wo ;

Zhou, Zhongyuan ;

Yu, Wing-Yiu .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) :2999-3006

[8] Pd-Catalyzed Ortho-C HAcylation/Cross Coupling of Aryl Ketone O-Methyl Oximes with Aldehydes Using tert-Butyl Hydroperoxide as Oxidant [J].

Chan, Chun-Wo ;

Zhou, Zhongyuan ;

Chan, Albert S. C. ;

Yu, Wing-Yiu .

ORGANIC LETTERS, 2010, 12 (17) :3926-3929

[9] Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter [J].

Chen, X ;

Li, JJ ;

Hao, XS ;

Goodhue, CE ;

Yu, JQ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :78-79

[10] PyDipSi: A General and Easily Modifiable/Traceless Si-Tethered Directing Group for C-H Acyloxylation of Arenes [J].

Chernyak, Natalia ;

Dudnik, Alexander S. ;

Huang, Chunhui ;

Gevorgyan, Vladimir .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) :8270-+

← 1 2 3 4 5 6 7 8 9 10 →