Premium
Lanthanide‐Catalyzed Tandem Insertion of Secondary Amines with 2‐Alkynylbenzonitriles: Synthesis of Aminoisoindoles
Author(s) -
Ye Pengqing,
Shao Yinlin,
Xie Leping,
Shen Keting,
Cheng Tianxing,
Chen Jiuxi
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201801252
Subject(s) - lanthanide , hydroamination , chemistry , tandem , catalysis , functional group , intermolecular force , combinatorial chemistry , medicinal chemistry , polymer chemistry , organic chemistry , molecule , ion , materials science , polymer , composite material
A lanthanide‐catalyzed intermolecular hydroamination of 2‐alkynylbenzonitriles with secondary amines has been disclosed, providing a streamlined access to a range of aminoisoindoles in moderate to excellent yields. The salient features of this reaction include high bond‐formation efficiency, mild reaction conditions, 100 % atomic efficiency and good functional group tolerance. This methodology has also been successfully applied to the construction of other nitrogen‐containing compounds, such as 5 H ‐imidazo[2,1‐ a ]isoindoles and isoquinolines. A plausible mechanism for the formation of aminoisoindoles involving initial N−H activation by a lanthanide complex followed by C≡N insertion into a Ln−N bond to form an amidinate lanthanide intermediate, which undergoes the cyclization is proposed.