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Angew Chem Int Ed Engl. 2014 Mar 3;53(10):2730-4. doi: 10.1002/anie.201308675. Epub 2014 Feb 2.

Direct synthesis of 1,4-diols from alkenes by iron-catalyzed aerobic hydration and C-H hydroxylation.

Author information

1
School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan).

Abstract

Various 1,4-diols are easily accessible from alkenes through iron-catalyzed aerobic hydration. The reaction system consists of a user-friendly iron phthalocyanine complex, sodium borohydride, and molecular oxygen. Furthermore, the effect of additional ligands on the iron complex was examined for a model reaction. The second hydroxy group is installed by direct C(sp(3))-H oxygenation, which is based on a [1,5] hydrogen shift process of a transient alkoxy radical that is formed by formal hydration of the olefin.

KEYWORDS:

CH oxygenation; iron catalysis; oxygen; radical reactions; synthetic methods

PMID:
24488606
DOI:
10.1002/anie.201308675
[Indexed for MEDLINE]

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