Electron-Transfer-Induced Intramolecular Heck Carbonylation Reactions Leading to Benzolactones and Benzolactams

Takahide Fukuyama; Takanobu Bando; Ilhyong Ryu

doi:10.1055/s-0037-1609964

Synthesis, Table of Contents

Synthesis 2018; 50(15): 3015-3021
DOI: 10.1055/s-0037-1609964

special topic

Electron-Transfer-Induced Intramolecular Heck Carbonylation Reactions Leading to Benzolactones and Benzolactams

Takahide Fukuyama

^aDepartment of Chemistry, Graduate School of Science, Osaka Prefecture University, 1-1 Gakuen-cho, Sakai, Osaka, 599-8531, Japan Email: ryu@c.s.osakafu-u.ac.jp

,

Takanobu Bando

^aDepartment of Chemistry, Graduate School of Science, Osaka Prefecture University, 1-1 Gakuen-cho, Sakai, Osaka, 599-8531, Japan Email: ryu@c.s.osakafu-u.ac.jp

,

Ilhyong Ryu*

^aDepartment of Chemistry, Graduate School of Science, Osaka Prefecture University, 1-1 Gakuen-cho, Sakai, Osaka, 599-8531, Japan Email: ryu@c.s.osakafu-u.ac.jp

^bDepartment of Applied Chemistry, National Chiao Tung University, 1001 University Road, Hsinchu, Taiwan

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Abstract

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Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis

Abstract

A metal-catalyst-free intramolecular Heck carbonylation reaction of benzyl alcohols and benzyl amines with carbon monoxide under heating at 250 °C affords the corresponding benzolactones and benzolactams in good to excellent yields. A hybrid radical/ionic chain mechanism, involving electron transfer from radical anions generated by nucleophilic attack of alcohols or amines on intermediate acyl radicals, is proposed.

Key words

carbonylation - electron transfer - radical reactions - metal-free - lactones - lactams

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References

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