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Iridium‐Catalyzed Annulation of Aromatic Imines with 1,3‐Dienes via Direct Functionalization of an Aromatic CH Bond
Author(s) -
Ebe Yusuke,
Hatano Miyuki,
Nishimura Takahiro
Publication year - 2015
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.201401171
Subject(s) - chemistry , annulation , iridium , aldimine , deprotonation , catalysis , medicinal chemistry , surface modification , diene , regioselectivity , metalation , combinatorial chemistry , organic chemistry , stereochemistry , ion , natural rubber
The [3+2] annulation of N ‐sulfonyl aromatic imines with 1,3‐dienes proceeded via a direct CH functionalization to give 1‐aminoindane derivatives in high yields with high regio‐ and stereoselectivities. The iridium complex coordinated with a substrate 1,3‐diene displayed high catalytic activity. The reaction proceeds via the direct formation of the aryliridium(I) species from the aromatic aldimine and an iridium(I) acetate species via a concerted metalation‐deprotonation pathway.