Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones

被引：50

作者：

Donohoe, Timothy J. ^{[1
]}

Pilgrim, Ben S. ^{[1
]}

Jones, Geraint R. ^{[1
]}

Bassuto, Jose A. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 2012年 / 109卷 / 29期

关键词：

alpha arylation; heterocycle; isoquinoline-N-oxide; one-pot; MEDIATED ELECTROPHILIC CYCLIZATION; AIR-STABLE CATALYSTS; ONE-POT SYNTHESIS; N-OXIDES; BENZODIAZEPINE-RECEPTORS; COUPLING REACTIONS; INTERNAL ALKYNES; ARYL HALIDES; INDOLES; COMPLEXES;

D O I：

10.1073/pnas.1206532109

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

The utilization of sequential palladium-catalyzed alpha-arylation and cyclization reactions provides a general approach to an array of isoquinolines and their corresponding N-oxides. This methodology allows the convergent combination of readily available precursors in a regioselective manner and in excellent overall yields. This powerful route to polysubstituted isoquinolines, which is not limited to electron rich moieties, also allows rapid access to analogues of biologically active compounds.

引用

页码：11605 / 11608

页数：4

共 50 条

[31] Palladium-Catalyzed Enantioselective α-Arylation of α-Fluoroketones [J].

Jiao, Zhiwei ;

Beiger, Jason J. ;

Jin, Yushu ;

Ge, Shaozhong ;

Zhou, Jianrong Steve ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (49) :15980-15986

[32] Palladium-Catalyzed Carbonylative Synthesis of Heterocycles [J].

Feng, Jian-Bo ;

Wu, Xiao-Feng .

HETEROCYCLIC CHEMISTRY IN THE 21ST CENTURY: A TRIBUTE TO ALAN KATRITZKY, 2017, 121 :207-246

[33] Palladium-Catalyzed α-Arylation of Arylketones at Low Catalyst Loadings [J].

Marelli, Enrico ;

Corpet, Martin ;

Davies, Sian R. ;

Nolan, Steven P. .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) :17272-17276

[34] Palladium-catalyzed desulfitative arylation of azoles with arylsulfonyl hydrazides [J].

Yu, Xinzhang ;

Li, Xingwei ;

Wan, Boshun .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (37) :7479-7482

[35] Palladium-Catalyzed Divergent Arylation of Triazolopyridines: AComputational Study [J].

AbuSalim, Deyaa I. ;

Hong, Sungwoo ;

Baik, Mu-Hyun .

CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) :2505-2510

[36] Palladium-Catalyzed Direct β-C-H Arylation of Ketones with Arylboronic Acids in Water [J].

Hu, Xiaoyun ;

Yang, Xiaobo ;

Dai, Xi-Jie ;

Li, Chao-Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (14) :2402-2406

[37] Exploration of Aryl Phosphates in Palladium-Catalyzed Mono-α-arylation of Aryl and Heteroaryl Ketones [J].

Chen, Xiangmeng ;

Chen, Zicong ;

So, Chau Ming .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10) :6337-6346

[38] Domino Rhodium-Catalyzed Alkyne Arylation/Palladium-Catalyzed N Arylation: A Mechanistic Investigation [J].

Panteleev, Jane ;

Zhang, Lei ;

Lautens, Mark .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9089-9092

[39] Palladium-Catalyzed Cascade Reaction for the Synthesis of Substituted Isoindolines [J].

Williams, Florence J. ;

Jarvo, Elizabeth R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (19) :4459-4462

[40] Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone [J].

Nambo, Masakazu ;

Crudden, Cathleen M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (03) :742-746

← 1 2 3 4 5 →