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

[21] Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].

Culkin, DA ;

Hartwig, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245

[22] Efficient synthesis of alkyl aryl ketones & ketals via palladium-catalyzed regioselective arylation of vinyl ethers [J].

Liu, Mingcui ;

Hyder, Zeynab ;

Sun, Yawei ;

Tang, Weijun ;

Xu, Lijin ;

Xiao, Jianliang .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (09) :2012-2015

[23] Ylide-Substituted Phosphines in Palladium-Catalyzed Coupling Reactions [J].

Knyszek, Daniel ;

Gessner, Viktoria H. .

ALDRICHIMICA ACTA, 2024, 57 (01)

[24] Surprising Reactivity in NiXantphos/Palladium-Catalyzed α-Arylation of Substituted Cyclopropyl Nitriles [J].

Wright, Brandon A. ;

Ardolino, Michael J. .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (08) :4670-4679

[25] Palladium-Catalyzed Direct Arylation of Free NH2-Substituted Thiophene Derivatives [J].

Derridj, Fazia ;

Roger, Julien ;

Djebbar, Safia ;

Doucet, Henri .

ORGANIC LETTERS, 2010, 12 (19) :4320-4323

[26] Palladium-catalyzed synthesis of vinyl phosphines from ketones [J].

Gilbertson, SR ;

Fu, Z ;

Starkey, GW .

TETRAHEDRON LETTERS, 1999, 40 (49) :8509-8512

[27] Palladium-Catalyzed α-Arylation of Vinylogous Esters for the Synthesis of γ,γ-Disubstituted Cyclohexenones [J].

Johnson, Thomas ;

Pultar, Felix ;

Menke, Friedericke ;

Lautens, Mark .

ORGANIC LETTERS, 2016, 18 (24) :6488-6491

[28] Palladium-Catalyzed Annulation of Acyloximes with Arynes (or Alkynes) Synthesis of Phenanthridines and Isoquinolines [J].

Gerfaud, Thibaud ;

Neuville, Luc ;

Zhu, Jieping .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) :572-577

[29] Palladium-Catalyzed α-Arylation of Benzylic Phosphonates [J].

Montel, Sonia ;

Raffier, Ludovic ;

He, Yuying ;

Walsh, Patrick J. .

ORGANIC LETTERS, 2014, 16 (05) :1446-1449

[30] Palladium-catalyzed Negishi α-arylation of alkylsulfones [J].

Zhou, Gang ;

Ting, Pauline C. ;

Aslanian, Robert G. .

TETRAHEDRON LETTERS, 2010, 51 (06) :939-941

← 1 2 3 4 5 →