Visible-light-promoted iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling in flow

Xiao Jing Wei; Irini Abdiaj; Carlo Sambiagio; Chenfei Li; Eli Zysman-Colman; Jesús Alcázar; Timothy Noël

doi:10.1002/anie.201906462

Visible-light-promoted iron-catalyzed C(sp²)–C(sp³) Kumada cross-coupling in flow

Xiao Jing Wei, Irini Abdiaj, Carlo Sambiagio, Chenfei Li, Eli Zysman-Colman, Jesús Alcázar, Timothy Noël (Corresponding author)

Micro Flow Chemistry and Synthetic Methodology

Research output: Contribution to journal › Article › Academic › peer-review

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Abstract

A continuous-flow, visible-light-promoted method has been developed to overcome the limitations of iron-catalyzed Kumada–Corriu cross-coupling reactions. A variety of strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at room temperature in high yields and within a few minutes’ residence time, considerably enhancing the applicability of this iron-catalyzed reaction. The robustness of this protocol was demonstrated on a multigram scale, thus providing the potential for future pharmaceutical application.

Original language	English
Pages (from-to)	13030-13034
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	37
DOIs	https://doi.org/10.1002/anie.201906462
Publication status	Published - 9 Sept 2019

Keywords

cross-coupling
flow chemistry
iron catalysis
Kumada coupling
photocatalysis

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10.1002/anie.201906462

Publishers versionFinal published version, 3.97 MBLicence: CC BY-NC-ND

Cite this

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title = "Visible-light-promoted iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling in flow",

abstract = "A continuous-flow, visible-light-promoted method has been developed to overcome the limitations of iron-catalyzed Kumada–Corriu cross-coupling reactions. A variety of strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at room temperature in high yields and within a few minutes{\textquoteright} residence time, considerably enhancing the applicability of this iron-catalyzed reaction. The robustness of this protocol was demonstrated on a multigram scale, thus providing the potential for future pharmaceutical application.",

keywords = "cross-coupling, flow chemistry, iron catalysis, Kumada coupling, photocatalysis",

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AU - Wei, Xiao Jing

AU - Abdiaj, Irini

AU - Sambiagio, Carlo

AU - Li, Chenfei

AU - Zysman-Colman, Eli

AU - Alcázar, Jesús

AU - Noël, Timothy

PY - 2019/9/9

Y1 - 2019/9/9

N2 - A continuous-flow, visible-light-promoted method has been developed to overcome the limitations of iron-catalyzed Kumada–Corriu cross-coupling reactions. A variety of strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at room temperature in high yields and within a few minutes’ residence time, considerably enhancing the applicability of this iron-catalyzed reaction. The robustness of this protocol was demonstrated on a multigram scale, thus providing the potential for future pharmaceutical application.

AB - A continuous-flow, visible-light-promoted method has been developed to overcome the limitations of iron-catalyzed Kumada–Corriu cross-coupling reactions. A variety of strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at room temperature in high yields and within a few minutes’ residence time, considerably enhancing the applicability of this iron-catalyzed reaction. The robustness of this protocol was demonstrated on a multigram scale, thus providing the potential for future pharmaceutical application.

KW - cross-coupling

KW - flow chemistry

KW - iron catalysis

KW - Kumada coupling

KW - photocatalysis

UR - https://www.scopus.com/pages/publications/85068901897

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DO - 10.1002/anie.201906462

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AN - SCOPUS:85068901897

SN - 1433-7851

VL - 58

SP - 13030

EP - 13034

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 37

ER -

Visible-light-promoted iron-catalyzed C(sp²)–C(sp³) Kumada cross-coupling in flow

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