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Sequential Organozinc Formation and Negishi Cross‐Coupling of Amides Catalysed by Cobalt Salt
Author(s) -
Dorval Céline,
Dubois Elodie,
BourneBranchu Yann,
Gosmini Corinne,
Danoun Grégory
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801577
Subject(s) - negishi coupling , chemistry , cobalt , amide , bromide , aryl , catalysis , salt (chemistry) , coupling (piping) , combinatorial chemistry , polymer chemistry , organic chemistry , materials science , metallurgy , alkyl
Herein, a cobalt‐catalysed Negishi‐type cross‐coupling of amide derivatives is described. Apart from being the first example of cobalt‐catalysed Negishi‐type coupling of amides, the process described employs a unique, simple, and cheap catalytic system to perform both the organozinc formation and the Negishi‐type coupling. Indeed, the same cobalt(II) bromide salt used to form the arylzinc species from aryl bromides is then re‐used to perform the cross coupling of this resulting arylzinc with N ‐benzoyl glutarimides at room temperature. The main advantages of the reaction presented are its robustness and ease of use. Indeed, the reactions of organozinc formation and Negishi‐type coupling are performed without precautions toward water or oxygen.