Nickel-Catalyzed Chemo- and Regioselective Arylcyanation of β,γ-Unsaturated Amides

A nickel-catalyzed intermolecular arylcyanation of 8-aminoquinolinyl β,γ-unsaturated amides is reported. The three-component reaction directly afforded diverse β-cyano γ-aryl amides with exclusive chemo- and regioselectivity. The synthetic practicality of this approach is further demonstrated throug...

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Published inOrganic letters Vol. 24; no. 24; pp. 4328 - 4332
Main Authors Hu, Jinghui, Du, Qiang, Zhao, Yao, Zhang, Fei, Chen, Rizhi, Zhou, Jianrong Steve, Wu, Xiaojin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.06.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALKENYL CARBONYL-COMPOUNDS
ENANTIOSELECTIVE CYANOFORMYLATION
NORBORNENE
CYANATION
OLEFINS
ARYL IODIDES
ALDEHYDES
ETHYL CYANOFORMATE
DICARBOFUNCTIONALIZATION
STRECKER REACTION
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Summary:A nickel-catalyzed intermolecular arylcyanation of 8-aminoquinolinyl β,γ-unsaturated amides is reported. The three-component reaction directly afforded diverse β-cyano γ-aryl amides with exclusive chemo- and regioselectivity. The synthetic practicality of this approach is further demonstrated through multigram scale reaction, expanded transformations of the nitrile product, late-stage modification of complex molecules, and direct drug synthesis.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01360