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Palladium‐Catalyzed Cycloisomerization of ( Z )‐1‐Iodo‐1,6‐dienes to 3‐Aza‐bicyclo[4.1.0]hept‐2‐enes
Author(s) -
Chi Xiaochen,
Meng Long,
Sun Xi,
Liu Qing,
Ai Bing,
Chen Lei,
Zhang Daopeng,
Zhao Pingping,
Dong Yunhui,
Liu Hui
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900079
Subject(s) - cycloisomerization , chemistry , bicyclic molecule , palladium , iodide , catalysis , alkyl , medicinal chemistry , stereochemistry , organic chemistry
A Pd‐catalyzed cycloisomerization of ( Z )‐1‐iodo‐1,6‐dienes was developed to construct 3‐aza‐bicyclo[4.1.0]hept‐2‐enes bearing substitutions at C1/C5. A wide array of ( Z )‐1‐iodo‐1,6‐dienes could be converted to the desired compounds efficiently. On the basis of mechanistic studies, two pathways were proposed, in which compound alkyl iodide derivatives formed by reductive elimination of C sp 3 −Pd−I was proved to be a possible intermediate.