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Issue 15, 2011
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Easy access to CF2-containing molecules based on the reaction of 2,2,3,3-tetrafluorooxetane with various nucleophiles

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Abstract

2,2,3,3-Tetrafluorooxetane reacted easily with organolithium reagents to give 1,1,3-trisubstituted 2,2-difluoropropan-1-ols in good to excellent yields. On the other hand, the reaction with Grignard reagent led to 3-bromo-1,1-disubstituted 2,2-difluoropropan-1-ols in good yields. On treating with lithium enolates, generated from enol silyl ethers and MeLi/LiBr, the corresponding 1-bromo-2,2-difluoro-3,5-dicarbonyl compounds were obtained in fair to good yields. 3-Iodo-2,2-difluoropropanoate, prepared readily from 2,2,3,3-tetrafluorooxetane and NaI, reacted successfully with various silyl enol ethers in the presence of a radical initiator to provide the corresponding coupling products in good yields.

Graphical abstract: Easy access to CF2-containing molecules based on the reaction of 2,2,3,3-tetrafluorooxetane with various nucleophiles

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Publication details

The article was received on 07 Apr 2011, accepted on 13 May 2011 and first published on 15 Jun 2011


Article type: Paper
DOI: 10.1039/C1OB05545C
Org. Biomol. Chem., 2011,9, 5493-5502

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    Easy access to CF2-containing molecules based on the reaction of 2,2,3,3-tetrafluorooxetane with various nucleophiles

    S. Yamada, M. Kato, Y. Komori, T. Konno and T. Ishihara, Org. Biomol. Chem., 2011, 9, 5493
    DOI: 10.1039/C1OB05545C

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