Regioselective Synthesis of γ-Lactones by Iron-Catalyzed Radical Annulation of Alkenes with α-Halocarboxylic Acids and Their Derivatives

Masayuki Iwasaki; Natsumi Miki; Yuichi Ikemoto; Yasuyuki Ura; Yasushi Nishihara

doi:10.1021/acs.orglett.8b01436

Regioselective Synthesis of γ-Lactones by Iron-Catalyzed Radical Annulation of Alkenes with α-Halocarboxylic Acids and Their Derivatives

Masayuki Iwasaki, Natsumi Miki, Yuichi Ikemoto, Yasuyuki Ura, Yasushi Nishihara

Research Institute for Interdisciplinary Science

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

19 Citations (Scopus)

Abstract

An abundant and low toxicity iron catalyst has enabled regioselective annulation of alkenes with α-halocarboxylic acids and their derivatives. The reaction proceeds smoothly without any additional ligands, bases, and additives to afford a variety of γ-lactones in good yields. A proposed reaction pathway through radical annulation is supported by some mechanistic studies, involving radical clock and isotope labeling experiments. The present method was applied to the practical iron-powder-promoted synthesis of γ-lactones.

Original language	English
Pages (from-to)	3848-3852
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.8b01436
Publication status	Published - Jul 6 2018

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Regioselective Synthesis of γ-Lactones by Iron-Catalyzed Radical Annulation of Alkenes with α-Halocarboxylic Acids and Their Derivatives",

abstract = "An abundant and low toxicity iron catalyst has enabled regioselective annulation of alkenes with α-halocarboxylic acids and their derivatives. The reaction proceeds smoothly without any additional ligands, bases, and additives to afford a variety of γ-lactones in good yields. A proposed reaction pathway through radical annulation is supported by some mechanistic studies, involving radical clock and isotope labeling experiments. The present method was applied to the practical iron-powder-promoted synthesis of γ-lactones.",

author = "Masayuki Iwasaki and Natsumi Miki and Yuichi Ikemoto and Yasuyuki Ura and Yasushi Nishihara",

note = "Funding Information: This work was partly supported by ACT-C, JST, as well as a Grant-in-Aid for Scientific Research (KAKENHI) (No. 16K17901) from JSPS. The authors gratefully thank Ms. Megumi Kosaka and Mr. Motonari Kobayashi (Department of Instrumental Analysis, Advanced Science Research Center, Okayama University) for performing elemental analyses, and the SC-NMR Laboratory (Okayama University) for the NMR spectral measurements.",

year = "2018",

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doi = "10.1021/acs.orglett.8b01436",

language = "English",

volume = "20",

pages = "3848--3852",

journal = "Organic Letters",

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T1 - Regioselective Synthesis of γ-Lactones by Iron-Catalyzed Radical Annulation of Alkenes with α-Halocarboxylic Acids and Their Derivatives

AU - Iwasaki, Masayuki

AU - Miki, Natsumi

AU - Ikemoto, Yuichi

AU - Ura, Yasuyuki

AU - Nishihara, Yasushi

N1 - Funding Information: This work was partly supported by ACT-C, JST, as well as a Grant-in-Aid for Scientific Research (KAKENHI) (No. 16K17901) from JSPS. The authors gratefully thank Ms. Megumi Kosaka and Mr. Motonari Kobayashi (Department of Instrumental Analysis, Advanced Science Research Center, Okayama University) for performing elemental analyses, and the SC-NMR Laboratory (Okayama University) for the NMR spectral measurements.

PY - 2018/7/6

Y1 - 2018/7/6

N2 - An abundant and low toxicity iron catalyst has enabled regioselective annulation of alkenes with α-halocarboxylic acids and their derivatives. The reaction proceeds smoothly without any additional ligands, bases, and additives to afford a variety of γ-lactones in good yields. A proposed reaction pathway through radical annulation is supported by some mechanistic studies, involving radical clock and isotope labeling experiments. The present method was applied to the practical iron-powder-promoted synthesis of γ-lactones.

AB - An abundant and low toxicity iron catalyst has enabled regioselective annulation of alkenes with α-halocarboxylic acids and their derivatives. The reaction proceeds smoothly without any additional ligands, bases, and additives to afford a variety of γ-lactones in good yields. A proposed reaction pathway through radical annulation is supported by some mechanistic studies, involving radical clock and isotope labeling experiments. The present method was applied to the practical iron-powder-promoted synthesis of γ-lactones.

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Regioselective Synthesis of γ-Lactones by Iron-Catalyzed Radical Annulation of Alkenes with α-Halocarboxylic Acids and Their Derivatives

Abstract

ASJC Scopus subject areas

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