Ruthenaelectro-Catalyzed Domino Three-Component Alkyne Annulation for Expedient Isoquinoline Assembly

Xuefeng Tan; Xiaoyan Hou; Torben Rogge; Lutz Ackermann

doi:10.1002/anie.202014289

Ruthenaelectro-Catalyzed Domino Three-Component Alkyne Annulation for Expedient Isoquinoline Assembly

Xuefeng Tan, Xiaoyan Hou, Torben Rogge, Lutz Ackermann^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

61 Citations (Scopus)

Abstract

The electrochemical three-component assembly of isoquinolines has been accomplished by ruthenaelectro-catalyzed C−H/N−H functionalization. The robustness of the electrocatalysis was reflected by an ample substrate scope, an efficient electrooxidation, and an operationally friendly procedure. The isolation of key intermediates and detailed mechanistic studies, including unprecedented cyclovoltammetric analysis of a seven-membered ruthenacycle, provided support for an unusual ruthenium(II/III/I) regime. © 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH

Original language	English
Pages (from-to)	4619-4624
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	9
Online published	3 Dec 2020
DOIs	https://doi.org/10.1002/anie.202014289
Publication status	Published - 23 Feb 2021
Externally published	Yes

Research Keywords

annulation
C−H activation
domino reactions
electrocatalysis
ruthenium

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10.1002/anie.202014289

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title = "Ruthenaelectro-Catalyzed Domino Three-Component Alkyne Annulation for Expedient Isoquinoline Assembly",

abstract = "The electrochemical three-component assembly of isoquinolines has been accomplished by ruthenaelectro-catalyzed C−H/N−H functionalization. The robustness of the electrocatalysis was reflected by an ample substrate scope, an efficient electrooxidation, and an operationally friendly procedure. The isolation of key intermediates and detailed mechanistic studies, including unprecedented cyclovoltammetric analysis of a seven-membered ruthenacycle, provided support for an unusual ruthenium(II/III/I) regime. {\textcopyright} 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH",

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author = "Xuefeng Tan and Xiaoyan Hou and Torben Rogge and Lutz Ackermann",

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day = "23",

doi = "10.1002/anie.202014289",

language = "English",

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T1 - Ruthenaelectro-Catalyzed Domino Three-Component Alkyne Annulation for Expedient Isoquinoline Assembly

AU - Tan, Xuefeng

AU - Hou, Xiaoyan

AU - Rogge, Torben

AU - Ackermann, Lutz

PY - 2021/2/23

Y1 - 2021/2/23

N2 - The electrochemical three-component assembly of isoquinolines has been accomplished by ruthenaelectro-catalyzed C−H/N−H functionalization. The robustness of the electrocatalysis was reflected by an ample substrate scope, an efficient electrooxidation, and an operationally friendly procedure. The isolation of key intermediates and detailed mechanistic studies, including unprecedented cyclovoltammetric analysis of a seven-membered ruthenacycle, provided support for an unusual ruthenium(II/III/I) regime. © 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH

AB - The electrochemical three-component assembly of isoquinolines has been accomplished by ruthenaelectro-catalyzed C−H/N−H functionalization. The robustness of the electrocatalysis was reflected by an ample substrate scope, an efficient electrooxidation, and an operationally friendly procedure. The isolation of key intermediates and detailed mechanistic studies, including unprecedented cyclovoltammetric analysis of a seven-membered ruthenacycle, provided support for an unusual ruthenium(II/III/I) regime. © 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH

KW - annulation

KW - C−H activation

KW - domino reactions

KW - electrocatalysis

KW - ruthenium

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UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-85100189600&origin=recordpage

U2 - 10.1002/anie.202014289

DO - 10.1002/anie.202014289

M3 - RGC 21 - Publication in refereed journal

C2 - 33270973

SN - 1433-7851

VL - 60

SP - 4619

EP - 4624

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 9

ER -

Ruthenaelectro-Catalyzed Domino Three-Component Alkyne Annulation for Expedient Isoquinoline Assembly

Abstract

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