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

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

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The first lactam-type 2-iodobenzamide catalysts, 8-iodoisoquinolinones 8 (IB-lactam) and 9 (MeO-IBlactam), 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.

Original language	English
Pages (from-to)	234-239
Number of pages	6
Journal	Chemical and Pharmaceutical Bulletin
Volume	72
Issue number	2
DOIs	https://doi.org/10.1248/cpb.c23-00887
State	Published - 2024

Keywords

Oxone
environmentally benign oxidation
hypervalent iodine
lactam
oxidation of alcohol

ASJC Scopus subject areas

General Chemistry
Drug Discovery

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10.1248/cpb.c23-00887

Cite this

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

abstract = "The first lactam-type 2-iodobenzamide catalysts, 8-iodoisoquinolinones 8 (IB-lactam) and 9 (MeO-IBlactam), 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.",

keywords = "Oxone, environmentally benign oxidation, hypervalent iodine, lactam, oxidation of alcohol",

author = "Takayuki Yakura and Tomoya Fujiwara and Kanna Asakubo and Perumalla, {Hema Naga Lakshmi} and Mitsuha Uzu and Takashi Okitsu and Kengo Kasama and Hisanori Nambu",

note = "Publisher Copyright: {\textcopyright} 2024 The Pharmaceutical Society of Japan.",

year = "2024",

doi = "10.1248/cpb.c23-00887",

language = "英語",

volume = "72",

pages = "234--239",

journal = "Chemical and Pharmaceutical Bulletin",

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publisher = "Pharmaceutical Society of Japan",

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TY - JOUR

T1 - 8-Iodoisoquinolinone, a Conformationally Rigid Highly Reactive 2-Iodobenzamide Catalyst for the Oxidation of Alcohols by Hypervalent Iodine

AU - Yakura, Takayuki

AU - Fujiwara, Tomoya

AU - Asakubo, Kanna

AU - Perumalla, Hema Naga Lakshmi

AU - Uzu, Mitsuha

AU - Okitsu, Takashi

AU - Kasama, Kengo

AU - Nambu, Hisanori

PY - 2024

Y1 - 2024

N2 - The first lactam-type 2-iodobenzamide catalysts, 8-iodoisoquinolinones 8 (IB-lactam) and 9 (MeO-IBlactam), 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.

AB - The first lactam-type 2-iodobenzamide catalysts, 8-iodoisoquinolinones 8 (IB-lactam) and 9 (MeO-IBlactam), 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.

KW - Oxone

KW - environmentally benign oxidation

KW - hypervalent iodine

KW - lactam

KW - oxidation of alcohol

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U2 - 10.1248/cpb.c23-00887

DO - 10.1248/cpb.c23-00887

M3 - 学術論文

C2 - 38417869

AN - SCOPUS:85186185701

SN - 0009-2363

VL - 72

SP - 234

EP - 239

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 2

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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