Palladium-Catalyzed C7-H (Hetero)arylation of Pyrazolo[1,5-a ]pyrazines with Heteroarenes and Aryl Iodides with the Assistance of Silver Salts

被引：2

作者：

Nguyen, Thanh V. Q. ^{[1
]}

Levoin, Armand ^{[1
,2
]}

Poli, Lorenzo ^{[1
,2
]}

机构：

[1] AstraZeneca, Med Chem Res & Early Dev Resp & Immunol, BioPharmaceut R&D, Gothenburg, Sweden

[2] Univ Strasbourg, 4 Rue Blaise Pascal, F-67081 Strasbourg, France

来源：

SYNTHESIS-STUTTGART | 2023年 / 55卷 / 21期

关键词：

C-H bond functionalization; fused-ring systems; heteroarenes; homogeneous catalysis; synthetic methods; H BOND FUNCTIONALIZATION; DIRECT ARYLATION; ACTIVATION; BROMIDES; TOOLS;

D O I：

10.1055/s-0041-1738433

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyrazolo[1,5-a]pyrazines coupled with heteroarenes and aryl iodides selectively at the C7 position to afford a broad library of bi(hetero)aryl structures under ligand-free palladium-catalyzed conditions. The key to the success of the reaction is the use of silver salts as the oxidant or the base, allowing the regioselective C-H bond functionalization to occur under relatively mild conditions.

引用

页码：3526 / 3534

页数：9

共 27 条

[21] Deuterium Exchange between Arenes and Deuterated Solvents in the Absence of a Transition Metal: Synthesis of D-Labeled Fluoroarenes [J].

Salamanca, Vanesa ;

Albeniz, Ana C. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (22) :3206-3212

[22] Pd-Catalyzed C-H arylation of pyridazine-based fused 1,2,4-triazoles: overriding selectivity at the usual position by undermining of preferred chelate formation [J].

Srinivasan, Ramasamy ;

Dey, Aniruddha ;

Nagarajan, N. Shanmugam ;

Kumaran, Rajendran Senthil ;

Gandhi, Thirumanavelan ;

Maiti, Debabrata .

CHEMICAL COMMUNICATIONS, 2017, 53 (85) :11709-11712

[23] Direct Arylation of Simple Arenes with Aryl Bromides by Synergistic Silver and Palladium Catalysis [J].

Tlahuext-Aca, Adrian ;

Lee, Sarah Yunmi ;

Sakamoto, Shu ;

Hartwig, John F. .

ACS CATALYSIS, 2021, 11 (03) :1430-1434

[24] Palladium-Catalyzed Regioselective Arylation of Pyrazolo[1,5-a]pyridines via C-H Activation and Synthetic Applications on P38 Kinase Inhibitors [J].

Wu, Hung -Chou ;

Chu, Jean-Ho ;

Li, Chin-Wei ;

Hwang, Long-Chih ;

Wu, Ming-Jung .

ORGANOMETALLICS, 2016, 35 (02) :288-300

[25] C-H Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals [J].

Yamaguchi, Junichiro ;

Yamaguchi, Atsushi D. ;

Itami, Kenichiro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) :8960-9009

[26] Construction of Biologically Important Biaryl Scaffolds through Direct C-H Bond Activation: Advances and Prospects [J].

Yuan, Shuo ;

Chang, Junbiao ;

Yu, Bin .

TOPICS IN CURRENT CHEMISTRY, 2020, 378 (02)

[27]

Zhang H.-H., 2022, SYNTHESIS-STUTTGART, V54, P4025

← 1 2 3 →