Premium
Use of a Readily Removable Auxiliary Group for the Synthesis of Pyrrolidones by the Palladium‐Catalyzed Intramolecular Amination of Unactivated γ C(sp 3 )H Bonds
Author(s) -
He Gang,
Zhang ShuYu,
Nack William A.,
Li Qiong,
Chen Gong
Publication year - 2013
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.201305615
Subject(s) - amination , palladium , ceric ammonium nitrate , intramolecular force , chemistry , catalysis , functional group , medicinal chemistry , ammonium , combinatorial chemistry , organic chemistry , polymer , grafting
Easy on, easy off : Directing groups found to promote the palladium‐catalyzed amination of γ C(sp 3 )H and C(sp 2 )H bonds of secondary amides included 5‐methoxy‐8‐aminoquinoline, which can be removed under mild conditions (see scheme; CAN=ceric ammonium nitrate). In conjunction with a β‐CH methylation or γ‐CH arylation step, the γ‐C(sp 3 )H amination provided access to complex pyrrolidones from readily available precursors.