Palladium catalyzed domino reaction of 1,4-disubstituted 1,2,3-triazoles via double C-H functionalization: one-pot synthesis of triazolo[1,5-f]phenanthridines

被引：28

作者：

Kumar, Avnish ^{[1
,2
]}

Shinde, Sundar S. ^{[1
,2
]}

Tiwari, Dharmendra Kumar ^{[1
]}

Sridhar, Balasubramanian ^{[3
]}

Likhar, Pravin R. ^{[1
,2
]}

机构：

[1] CSIR Indian Inst Chem Technol, Inorgan & Phys Chem Div, Organometall Gp, Hyderabad 500007, Andhra Pradesh, India

[2] CSIR Indian Inst Chem Technol, Acad Sci & Innovat Res AcSIR, Hyderabad 500007, Andhra Pradesh, India

[3] CSIR Indian Inst Chem Technol, Xray Crystall Ctr, Hyderabad 500007, Andhra Pradesh, India

来源：

RSC ADVANCES | 2016年 / 6卷 / 49期

关键词：

FACILE SYNTHESIS; BOND FORMATION; DERIVATIVES; CONSTRUCTION; ACTIVATION; ARYLATION; ARYL; DIFUNCTIONALIZATION; ALKYLATION; ROUTE;

D O I：

10.1039/c6ra06755g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium catalyzed domino coupling reaction of 1,4-disubstituted triazoles via homocondensation with a second molecule is presented. The domino couplings involve the formation of biaryl and bi(hetero)aryl bonds through a five membered carbopalladacycle intermediate. The approach provides a simple, straight forward and facile route to access triazolo[1,5-f]phenanthridines in high yields. Furthermore, the developed protocol was extended to heterocondensation in the presence of norbornene.

引用

收藏

页码：43638 / 43647

页数：10

相关论文

共 63 条

[1] OXIMES OF FIVE-MEMBERED HETEROCYCLIC COMPOUNDS WITH THREE AND FOUR HETEROATOMS 2. SYNTHESIS OF DERIVATIVES, REACTIONS, AND BIOLOGICAL ACTIVITY (REVIEW) [J].

Abele, E. ;

Abele, R. ;

Lukevics, E. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (07) :769-792

[2] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[3] Regioselective syntheses of fully-substituted 1,2,3-triazoles: the CuAAC/C-H bond functionalization nexus [J].

Ackermann, Lutz ;

Potukuchi, Harish Kumar .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4503-4513

[4] Palladium-Catalyzed Dehydrogenative Direct Arylations of 1,2,3-Triazoles [J].

Ackermann, Lutz ;

Jeyachandran, Rajkumar ;

Potukuchi, Harish K. ;

Novak, Petr ;

Buettner, Lea .

ORGANIC LETTERS, 2010, 12 (09) :2056-2059

[5] Recent advances in heterobimetallic palladium(II)/copper(II) catalyzed domino difunctionalization of carbon-carbon multiple bonds [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Gazzola, Silvia ;

Mazza, Alberto .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (35) :6767-6789

[6] Intramolecular Palladium-Catalyzed Aminocarboxylation of Olefins as a Direct Route to Bicyclic Oxazolidinones [J].

Borsini, Elena ;

Broggini, Gianluigi ;

Fasana, Andrea ;

Galli, Simona ;

Khansaa, Maisaa ;

Piarulli, Umberto ;

Rigamonti, Micol .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (06) :985-994

[7] Selective Intramolecular Palladium(II)-Catalyzed Aminooxygenation vs. Diamination of Alkenylureas: Efficient Microwave-Assisted Reactions to Bicyclic Piperazinones [J].

Broggini, Gianluigi ;

Barbera, Vincenzina ;

Beccalli, Egle M. ;

Chiacchio, Ugo ;

Fasana, Andrea ;

Galli, Simona ;

Gazzola, Silvia .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (08) :1640-1648

[8] Pd-Catalyzed cyclization reaction: a convenient domino process for synthesis of α-carbonyl furan derivatives [J].

Cao, Hua ;

Jiang, Huan-Feng ;

Huang, Hua-Wen ;

Zhao, Jin-Wu .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (21) :7313-7317

[9] SOME PALLADIUM-CATALYZED CARBON CARBON BOND FORMATION REACTIONS [J].

CATELLANI, M ;

CHIUSOLI, GP ;

COSTA, M .

PURE AND APPLIED CHEMISTRY, 1990, 62 (04) :623-630

[10]

Chen X., 2009, ANGEW CHEM, V121, P5196

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