8-Iodoisoquinolinone, a Conformationally Rigid Highly Reactive 2-Iodobenzamide Catalyst for the Oxidation of Alcohols by Hypervalent Iodine

Takayuki Yakura; Tomoya Fujiwara; Kanna Asakubo; Hema Naga Lakshmi Perumalla; Mitsuha Uzu; Takashi Okitsu; Kengo Kasama; Hisanori Nambu

doi:10.1248/cpb.c23-00887

Regular Article

8-Iodoisoquinolinone, a Conformationally Rigid Highly Reactive 2-Iodobenzamide Catalyst for the Oxidation of Alcohols by Hypervalent Iodine

Takayuki Yakura , Tomoya Fujiwara, Kanna Asakubo, Hema Naga Lakshmi Perumalla, Mitsuha Uzu, Takashi Okitsu, Kengo Kasama, Hisanori Nambu

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Keywords: environmentally benign oxidation, hypervalent iodine, lactam, Oxone, oxidation of alcohol

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Supplementary material

2024 Volume 72 Issue 2 Pages 234-239

DOI https://doi.org/10.1248/cpb.c23-00887

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Abstract

The first lactam-type 2-iodobenzamide catalysts, 8-iodoisoquinolinones 8 (IB-lactam) and 9 (MeO-IB-lactam), were developed. These catalysts have a conformationally rigid 6/6 bicyclic lactam structure and are more reactive than the previously reported catalysts 2-iodobenzamides 4 (IBamide) and 5 (MeO-IBamide) for the oxidation of alcohols. The lactam structure could form an efficient intramolecular I---O interaction, depending on the size of the lactam ring.

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