Nucleophilic fluoroalkylation/cyclization route to fluorinated phthalides

Masanori Inaba; Tatsuya Sakai; Shun Shinada; Tsuyuka Sugiishi; Yuta Nishina; Norio Shibata; Hideki Amii

doi:10.3762/bjoc.14.12

Nucleophilic fluoroalkylation/cyclization route to fluorinated phthalides

Masanori Inaba, Tatsuya Sakai, Shun Shinada, Tsuyuka Sugiishi, Yuta Nishina, Norio Shibata, Hideki Amii

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Abstract

Discribed in this article is a versatile and practical method for the synthesis of C3-perfluoroalkyl-substituted phthalides in a one-pot manner. Upon treatment of KF or triethylamine, 2-cyanobenzaldehyde reacted with (perfluoroalkyl)trimethylsilanes via nucleophilic addition and subsequent intramolecular cyclization to give perfluoroalkylphthalides in good yields.

Original language	English
Pages (from-to)	182-186
Number of pages	5
Journal	Beilstein Journal of Organic Chemistry
Volume	14
DOIs	https://doi.org/10.3762/bjoc.14.12
Publication status	Published - Jan 19 2017

Keywords

Cyclization
Fluorine
Lactone
Phthalide
Trifluoromethylation

ASJC Scopus subject areas

Organic Chemistry

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Inaba, M., Sakai, T., Shinada, S., Sugiishi, T., Nishina, Y., Shibata, N., & Amii, H. (2017). Nucleophilic fluoroalkylation/cyclization route to fluorinated phthalides. Beilstein Journal of Organic Chemistry, 14, 182-186. https://doi.org/10.3762/bjoc.14.12

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AU - Inaba, Masanori

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AU - Nishina, Yuta

AU - Shibata, Norio

AU - Amii, Hideki

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AB - Discribed in this article is a versatile and practical method for the synthesis of C3-perfluoroalkyl-substituted phthalides in a one-pot manner. Upon treatment of KF or triethylamine, 2-cyanobenzaldehyde reacted with (perfluoroalkyl)trimethylsilanes via nucleophilic addition and subsequent intramolecular cyclization to give perfluoroalkylphthalides in good yields.

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KW - Phthalide

KW - Trifluoromethylation

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