Cobalt(II) catalyzed C(sp)-H bond functionalization of alkynes with phenyl hydrazines: facile access to diaryl 1,2-diketones

被引：29

作者：

Bharate, Jaideep B. ^{[1
,2
]}

Abbat, Sheenu ^{[3
,4
]}

Sharma, Rohit ^{[1
,2
]}

Bharatam, Prasad V. ^{[3
,4
]}

Vishwakarma, Ram A. ^{[1
,2
]}

Bharate, Sandip B. ^{[1
,2
]}

机构：

[1] CSIR Indian Inst Integrat Med, Div Med Chem, Jammu 180001, India

[2] CSIR Indian Inst Integrat Med, Acad Sci & Innovat Res AcSIR, Jammu 180001, India

[3] NIPER, Dept Pharmacoinformat, Sas Nagar 160062, Punjab, India

[4] NIPER, Dept Med Chem, Sas Nagar 160062, Punjab, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 18期

关键词：

ROOM-TEMPERATURE; C-C; EFFICIENT SYNTHESIS; AEROBIC OXIDATION; ARYLATION; DERIVATIVES; ACTIVATION; ALCOHOLS; CLEAVAGE; ALKENES;

D O I：

10.1039/c5ob00419e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cobalt acetylacetonate catalyzed oxidative diketonation of alkynes via C(sp)-H bond functionalization has been described. The reaction involves a free-radical mechanism, wherein the phenyl radical formed from phenyl hydrazine couples with Co(II) activated alkyne to produce 1,2-diketones. The reaction proceeds at room temperature in DMF with the use of Ag2O/air as the oxidizing system. The utility of the protocol for the synthesis of a series of imidazoles including a potent platelet aggregation inhibitor trifenagrel has been demonstrated.

引用

页码：5235 / 5242

页数：8

共 46 条

[1]

ABRAHAMS SL, 1989, J PHARMACOL EXP THER, V249, P359

[2] ONE-STEP SYNTHESIS OF 1,N-DICARBONYL COMPOUNDS FROM CARBOXYLIC-ACID DERIVATIVES AND DI-GRIGNARD REAGENTS IN THE PRESENCE OF TRANSITION-METAL CATALYSTS [J].

BABUDRI, F ;

DETTOLE, A ;

FIANDANESE, V ;

MARCHESE, G ;

NASO, F .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 405 (01) :53-58

[3] Antiinflammatory 4,5-diarylimidazoles as selective cyclooxygenase inhibitors [J].

Barta, TE ;

Stealey, MA ;

Collins, PW ;

Weier, RM .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (24) :3443-3448

[4] Synthetic Routes to N-Heterocyclic Carbene Precursors [J].

Benhamou, Laure ;

Chardon, Edith ;

Lavigne, Guy ;

Bellemin-Laponnaz, Stephane ;

Cesar, Vincent .

CHEMICAL REVIEWS, 2011, 111 (04) :2705-2733

[5] An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst [J].

Bhosale, RS ;

Sarda, SR ;

Ardhapure, SS ;

Jadhav, WN ;

Bhusare, SR ;

Pawar, RP .

TETRAHEDRON LETTERS, 2005, 46 (42) :7183-7186

[6] Synthesis of 2,4,5-triarylimidazoles in aqueous solution, under microwave irradiation [J].

Chauveau, Edouard ;

Marestin, Catherine ;

Schiets, Frederic ;

Mercier, Regis .

GREEN CHEMISTRY, 2010, 12 (06) :1018-1022

[7] Ruthenium-Catalyzed Oxidation of Alkenes at Room Temperature: A Practical and Concise Approach to α-Diketones [J].

Chen, Shulin ;

Liu, Zhaojun ;

Shi, Erbo ;

Chen, Long ;

Wei, Wei ;

Li, Hong ;

Cheng, Yannan ;

Wan, Xiaobing .

ORGANIC LETTERS, 2011, 13 (09) :2274-2277

[8] Phenyl Hydrazine as Initiator for Direct Arene C-H Arylation via Base Promoted Homolytic Aromatic Substitution [J].

Dewanji, Abhishek ;

Murarka, Sandip ;

Curran, Dennis P. ;

Studer, Armido .

ORGANIC LETTERS, 2013, 15 (23) :6102-6105

[9] Hydrazone Radical Promoted Vicinal Difunctionalization of Alkenes and Trifunctionalization of Allyls: Synthesis of Pyrazolines and Tetrahydropyridazines [J].

Duan, Xiao-Yong ;

Yang, Xiu-Long ;

Fang, Ran ;

Peng, Xie-Xue ;

Yu, Wei ;

Han, Bing .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (21) :10692-10704

[10] Spectroscopic study of 2-, 4-and 5-substituents on pKa values of imidazole heterocycles prone to intramolecular proton-electrons transfer [J].

Eseola, Abiodun O. ;

Obi-Egbedi, Nelson O. .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2010, 75 (02) :693-701

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