A New Method for the Synthesis of 1,4-Diols: C(sp3)–H Hydroxylation Induced by Iron-Catalyzed Redox Hydration of Alkenes

Tsuyoshi Taniguchi; Daisuke Hirose; Takuma Hashimoto

doi:10.1055/s-0034-1379214

Synlett, Table of Contents

Synlett 2014; 25(18): 2531-2535
DOI: 10.1055/s-0034-1379214

synpacts

A New Method for the Synthesis of 1,4-Diols: C(sp³)–H Hydroxylation Induced by Iron-Catalyzed Redox Hydration of Alkenes

Authors

Tsuyoshi Taniguchi*

^aSchool of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan Fax: +81(76)2344439 Email: tsuyoshi@p.kanazawa-u.ac.jp
Daisuke Hirose

^bGraduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
Takuma Hashimoto

^aSchool of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan Fax: +81(76)2344439 Email: tsuyoshi@p.kanazawa-u.ac.jp

Abstract

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Abstract

A novel method for the synthesis of 1,4-diols from alkenes is presented. The reaction is the basis of iron-catalyzed redox hydration of alkenes. The second hydroxyl group is introduced by hydroxylation of an inert C–H bond. The mechanism includes a radical 1,5-hydrogen-transfer process of an intermediary alkoxy radical. In this paper, we describe how this new method has been discovered and developed.

Key words

alkenes - hydroxylation - iron - oxygen - radicals

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References

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