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Cobalt‐Catalyzed Electrophilic Amination of Aryl‐ and Heteroarylzinc Pivalates with N ‐Hydroxylamine Benzoates
Author(s) -
Chen YiHung,
Graßl Simon,
Knochel Paul
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201710931
Subject(s) - amination , electrophilic amination , aryl , chemistry , cobalt , benzoates , electrophile , yield (engineering) , hydroxylamine , catalysis , organic chemistry , medicinal chemistry , combinatorial chemistry , alkyl , materials science , metallurgy
Aryl‐ and heteroarylzinc pivalates can be aminated with O ‐benzoylhydroxylamines at 25 °C within 2–4 h in the presence of 2.5–5.0 % CoCl 2 ⋅2 LiCl to furnish the corresponding tertiary arylated or heteroarylated amines in good yields. This electrophilic amination also provides access to diarylamines and aryl(heteroaryl)amines. A new tuberculosis drug candidate (Q203) was prepared in six steps and 56 % overall yield by using this cobalt‐catalyzed amination as the key step.