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Recent Achievements in the Rhodium‐Catalyzed Concise Construction of Medium N‐Heterocycles, Azepines and Azocines
Author(s) -
Ouyang Wensen,
Rao Jianhang,
Li Yibiao,
Liu Xiaohang,
Huo Yanping,
Chen Qian,
Li Xianwei
Publication year - 2020
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.202001040
Subject(s) - rhodium , chemistry , nitrene , carbenoid , cycloisomerization , context (archaeology) , catalysis , combinatorial chemistry , ring (chemistry) , total synthesis , organic chemistry , paleontology , biology
Medium N‐heterocycles, azepines and azocines, serve as important skeletons that occurred widely in natural products, however, due to the lack of efficient synthetic methodologies, their application potential in biologically active molecules, pharmaceuticals and agrochemicals remained to be explored. In this context, rhodium catalysis in this field featured good reactivity and functional group tolerance, with readily available starting materials, and enabled rapid access to the azepines and azocines. Delightfully, great achievements in the concise construction of these 7 and 8‐membered N‐heterocycles under rhodium catalysis have been made, which mainly included cycloisomerization of unsaturated C−X bonds (which might also combine the ring‐opening strategy on strained rings), metal carbenoid or nitrene insertion involved transformations and direct C−H activation reactions. Considering the great performance of rhodium catalyst in the synthesis of azepines and azocines, herein, we summarized the recent results in this field, and wish to give further insight and inspired more encouraging methodologies and new drug discovery based on these 7 and 8‐membered N‐heterocycles.