An efficient low-temperature route to polycyclic isoquinoline salt synthesis via C-H activation with [Cp*MCl2]2 (M = Rh, Ir).

作者: Ling Li , William W. Brennessel , William D. Jones

DOI: 10.1021/JA802415H

关键词: IsoquinolineMedicinal chemistryOxidative coupling of methaneChemistrySodium acetateOrganic chemistryAlkyneSalt (chemistry)

摘要: Bi-, tri-, and tetracyclic isoquinoline salts were readily synthesized in excellent yields at room temperature from available starting materials after three reaction steps. Aromatic C−H activation was first promoted by sodium acetate with [Cp*MCl2]2 (M = Rh, Ir) to form cyclometalated compounds. Dimethylacetylenedicarboxylate then found insert into the metal−carbon bonds of Finally, insertion compounds underwent oxidative coupling desired regenerate [Cp*MCl2]2. All intermediate following activation, alkyne insertion, fully characterized, including determination X-ray structures several cases, results shed light on overall mechanism. Moreover, it possible synthesize using one-pot procedures; thus, this work provides a novel, efficient method for metal-mediated syn...

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