Metallaphotoredox-Mediated Csp2-H Hydroxylation of Arenes under Aerobic Conditions

被引：39

作者：

Shah, Sk Sheriff ^{[1
]}

Paul, Amrita ^{[1
]}

Bera, Manoranjan ^{[1
]}

Venkatesh, Yarra ^{[1
]}

Singh, N. D. Pradeep ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 18期

关键词：

C-H ARYLATION; VISIBLE-LIGHT PHOTOCATALYSIS; PHOTOREDOX CATALYSIS; DUAL CATALYSIS; LIGAND; FUNCTIONALIZATION; ACTIVATION; OXIDATION; SALTS; OXYGENATION;

D O I：

10.1021/acs.orglett.8b01973

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct hydroxylation of 2-arylpyridines and 2-arylbenzothiazoles via the merger of organic photoredox and metal catalysis is reported where 4CzIPN is used as the visible-light photocatalyst and Pd(OAc)(2) as the metal catalyst. This method has been employed to synthesize organic molecules exhibiting excited-state intramolecular proton transfer properties for generating tunable luminescence responses.

引用

页码：5533 / 5536

页数：4

共 44 条

[1] Transition-Metal-Catalyzed Synthesis of Hydroxylated Arenes [J].

Alonso, Diego A. ;

Najera, Carmen ;

Pastor, Isidro M. ;

Yus, Miguel .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (18) :5274-5284

[2] A p-Hydroxyphenacyl-Benzothiazole-Chlorambucil Conjugate as a Real-Time-Monitoring Drug-Delivery System Assisted by Excited-State Intramolecular Proton Transfer [J].

Barman, Shrabani ;

Mukhopadhyay, Sourav K. ;

Biswas, Sandipan ;

Nandi, Surajit ;

Gangopadhyay, Moumita ;

Dey, Satyahari ;

Anoop, Anakuthil ;

Singh, N. D. Pradeep .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (13) :4194-4198

[3] Palladium-Catalyzed ortho-CH-Bond Oxygenation of Aromatic Ketones [J].

Choy, Pui Ying ;

Kwong, Fuk Yee .

ORGANIC LETTERS, 2013, 15 (02) :270-273

[4] Mechanism of the Palladium-Catalyzed Arene C-H Acetoxylation: A Comparison of Catalysts and Ligand Effects [J].

Cook, Amanda K. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (08) :3109-3118

[5] Aryl amination using ligand-free Ni(II) salts and photoredox catalysis [J].

Corcoran, Emily B. ;

Pirnot, Michael T. ;

Lin, Shishi ;

Dreher, Spencer D. ;

DiRocco, Daniel A. ;

Davies, Ian W. ;

Buchwald, Stephen L. ;

MacMillan, David W. C. .

SCIENCE, 2016, 353 (6296) :279-283

[6] Photoinduced Ullmann C-N Coupling: Demonstrating the Viability of a Radical Pathway [J].

Creutz, Sidney E. ;

Lotito, Kenneth J. ;

Fu, Gregory C. ;

Peters, Jonas C. .

SCIENCE, 2012, 338 (6107) :647-651

[7] Visible-light-mediated conversion of alcohols to halides [J].

Dai, Chunhui ;

Narayanam, Jagan M. R. ;

Stephenson, Corey R. J. .

NATURE CHEMISTRY, 2011, 3 (02) :140-145

[8] Aerobic Direct C(sp2)-H Hydroxylation of 2-Arylpyridines by Palladium Catalysis Induced with Aldehyde Auto-Oxidation [J].

Das, Prasenjit ;

Saha, Debajyoti ;

Saha, Dibyajyoti ;

Guin, Joyram .

ACS CATALYSIS, 2016, 6 (09) :6050-6054

[9] Synthetic and Mechanistic Studies of Pd-Catalyzed C-H Arylation with Diaryliodonium Salts: Evidence for a Bimetallic High Oxidation State Pd Intermediate [J].

Deprez, Nicholas R. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) :11234-11241

[10] A highly selective catalytic method for the oxidative functionalization of C-H bonds [J].

Dick, AR ;

Hull, KL ;

Sanford, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2300-2301

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