Synthesis of 2,2-difluoro-homoallylic alcohols via ring-opening of gem-difluorocyclopropane and aerobic oxidation by photo-irradiation in the presence of an organic pigment

Hiroaki Takenaka; Yoshihiro Masuhara; Kent Narita; Toshiki Nokami; Toshiyuki Itoh

doi:10.1039/C8OB01740A

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Synthesis of 2,2-difluoro-homoallylic alcohols via ring-opening of gem-difluorocyclopropane and aerobic oxidation by photo-irradiation in the presence of an organic pigment†

Hiroaki Takenaka,^a Yoshihiro Masuhara,^a Kent Narita,^a Toshiki Nokami

^ab and Toshiyuki Itoh

*^ab

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* Corresponding authors

^a Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, Tottori 680-8552, Japan
E-mail: titoh@tottori-u.ac.jp
Fax: +81-857-31-5259
Tel: +81-857-31-5259

^b Centre for Research on Green Sustainable Chemistry, Tottori University, Japan

Abstract

We found that aerobic oxidation took place after the visible light-mediated ring-opening reaction of gem-difluorocyclopropane in the presence of an organic dye and amine to furnish 2,2-difluoro-homoallylic alcohols in good yields.

This article is part of the themed collections: Synthetic methodology in OBC and Fluorine Chemistry

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Article information

DOI: https://doi.org/10.1039/C8OB01740A
Article type: Paper
Submitted: 20 iyl 2018
Accepted: 06 avq 2018
First published: 06 avq 2018

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Org. Biomol. Chem., 2018,16, 6106-6114

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Synthesis of 2,2-difluoro-homoallylic alcohols via ring-opening of gem-difluorocyclopropane and aerobic oxidation by photo-irradiation in the presence of an organic pigment

H. Takenaka, Y. Masuhara, K. Narita, T. Nokami and T. Itoh, Org. Biomol. Chem., 2018, 16, 6106 DOI: 10.1039/C8OB01740A

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Organic & Biomolecular Chemistry

Synthesis of 2,2-difluoro-homoallylic alcohols via ring-opening of gem-difluorocyclopropane and aerobic oxidation by photo-irradiation in the presence of an organic pigment†

Abstract

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Synthesis of 2,2-difluoro-homoallylic alcohols via ring-opening of gem-difluorocyclopropane and aerobic oxidation by photo-irradiation in the presence of an organic pigment

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