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Synthesis of Isoquinolines via Rhodium(III)-Catalyzed Dehydrative CC and CN Coupling between Oximines and Alkynes

✍ Scribed by Xingping Zhang; Dan Chen; Miao Zhao; Jing Zhao; Aiqun Jia; Xingwei Li

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 193 KB
Volume: 353
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.201000887

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✦ Synopsis

Abstract

Isoquinolines have been synthesized from the redox‐neutral dehydrative CN and CC cross‐coupling between oximines and alkynes using a catalytic amount of (pentamethylcyclopentadiene)rhodium dichloride dimer {[RhCp*Cl~2~]~2~} and cesium acetate (CsOAc), a process that involves ortho CH activation of oximines and subsequent functionalization with alkynes. This redox‐neutral catalytic isoquinoline synthesis operates under mild conditions, and is insensitive to moisture or air. A broad scope of coupling partners has been established, and a likely mechanism has been suggested.

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