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Unusual Skeletal Reorganization of Oxetanes for the Synthesis of 1,2‐Dihydroquinolines
Author(s) -
Wang Guannan,
Huang Hai,
Guo Wengang,
Qian Chenxiao,
Sun Jianwei
Publication year - 2020
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.201916727
Subject(s) - oxetane , chemistry , molecule , catalysis , cleavage (geology) , combinatorial chemistry , polymer chemistry , organic chemistry , materials science , fracture (geology) , composite material
Skeletal reorganization is a type of fascinating transformations owing to their intriguing mechanisms and utility in complex molecule synthesis. However, only a limited amount of examples are known for most functional groups. Herein, we describe such an unusual process of oxetanes. In the presence of In(OTf) 3 as catalyst, oxetane‐tethered anilines reacted unexpectedly to form 1,2‐dihydroquinolines. This process not only provides expedient access to dihydroquinolines, but also represents a new reaction of oxetane. Mechanistically, it is believed that the reaction proceeds through initial nitrogen attack rather than arene attack followed by a series of bond cleavage and formation events. Control experiments provided important insights into the mechanism.