Synthesis of Biaryls through Nickel-Catalyzed Suzuki-Miyaura Coupling of Amides by Carbon-Nitrogen Bond Cleavage

The first Ni‐catalyzed Suzuki–Miyaura coupling of amides for the synthesis of widely occurring biaryl compounds through N−C amide bond activation is reported. The reaction tolerates a wide range of electron‐withdrawing, electron‐neutral, and electron‐donating substituents on both coupling partners....

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-06, Vol.55 (24), p.6959-6963
Main Authors: Shi, Shicheng, Meng, Guangrong, Szostak, Michal
Format: Article
Language:English
Subjects:
amide bonds
biaryls
cross-coupling
nickel
N−C activation
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Summary:The first Ni‐catalyzed Suzuki–Miyaura coupling of amides for the synthesis of widely occurring biaryl compounds through N−C amide bond activation is reported. The reaction tolerates a wide range of electron‐withdrawing, electron‐neutral, and electron‐donating substituents on both coupling partners. The reaction constitutes the first example of the Ni‐catalyzed generation of aryl electrophiles from bench‐stable amides with potential applications for a broad range of organometallic reactions. Breaking and making: The first nickel‐catalyzed Suzuki–Miyaura coupling of amides for the synthesis of biaryl compounds through N−C amide bond cleavage is reported. The reaction tolerates a wide range of sensitive and electronically diverse substituents on both coupling partners.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201601914