Iridium‐Catalyzed Annulation of Aromatic Imines with 1,3‐Dienes  via  Direct Functionalization of an Aromatic CH Bond | Zendy

Ebe Yusuke | Zendy; Hatano Miyuki | Zendy; Nishimura Takahiro | Zendy

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Iridium‐Catalyzed Annulation of Aromatic Imines with 1,3‐Dienes via Direct Functionalization of an Aromatic CH 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.

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