Nucleophilic trifluoromethylation of anhydrides employing (trifluoromethyl)trimethylsilane: Synthesis of γ-trifluoromethylated γ-butyrolactones

Chonticha Masusai; Darunee Soorukram; Chutima Kuhakarn; Patoomratana Tuchinda; Vichai Reutrakul; Manat Pohmakotr

doi:10.1016/j.jfluchem.2013.06.006

Nucleophilic trifluoromethylation of anhydrides employing (trifluoromethyl)trimethylsilane: Synthesis of γ-trifluoromethylated γ-butyrolactones

Chonticha Masusai
, Darunee Soorukram
, Chutima Kuhakarn
, Patoomratana Tuchinda
, Vichai Reutrakul
, Manat Pohmakotr

Mahidol University

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

Fluoride-catalyzed nucleophilic trifluoromethylation of acid anhydrides using CF3SiMe3 provided the corresponding γ-hydroxy-γ- trifluoromethyl-γ-butyrolactones. The utility of these adducts was further demonstrated by treatment with Grignard reagents, leading to γ-trifluoromethylated γ-butyrolactones.

Original language	English
Pages (from-to)	37-42
Number of pages	6
Journal	Journal of Fluorine Chemistry
Volume	154
DOIs	https://doi.org/10.1016/j.jfluchem.2013.06.006
Publication status	Published - 2013
Externally published	Yes

Keywords

Anhydrides
Ruppert-Prakash reagent
Trifluoromethylation
γ-Butyrolactones

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10.1016/j.jfluchem.2013.06.006

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title = "Nucleophilic trifluoromethylation of anhydrides employing (trifluoromethyl)trimethylsilane: Synthesis of γ-trifluoromethylated γ-butyrolactones",

abstract = "Fluoride-catalyzed nucleophilic trifluoromethylation of acid anhydrides using CF3SiMe3 provided the corresponding γ-hydroxy-γ- trifluoromethyl-γ-butyrolactones. The utility of these adducts was further demonstrated by treatment with Grignard reagents, leading to γ-trifluoromethylated γ-butyrolactones.",

keywords = "Anhydrides, Ruppert-Prakash reagent, Trifluoromethylation, γ-Butyrolactones",

author = "Chonticha Masusai and Darunee Soorukram and Chutima Kuhakarn and Patoomratana Tuchinda and Vichai Reutrakul and Manat Pohmakotr",

year = "2013",

doi = "10.1016/j.jfluchem.2013.06.006",

language = "English",

volume = "154",

pages = "37--42",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - Nucleophilic trifluoromethylation of anhydrides employing (trifluoromethyl)trimethylsilane

T2 - Synthesis of γ-trifluoromethylated γ-butyrolactones

AU - Masusai, Chonticha

AU - Soorukram, Darunee

AU - Kuhakarn, Chutima

AU - Tuchinda, Patoomratana

AU - Reutrakul, Vichai

AU - Pohmakotr, Manat

PY - 2013

Y1 - 2013

N2 - Fluoride-catalyzed nucleophilic trifluoromethylation of acid anhydrides using CF3SiMe3 provided the corresponding γ-hydroxy-γ- trifluoromethyl-γ-butyrolactones. The utility of these adducts was further demonstrated by treatment with Grignard reagents, leading to γ-trifluoromethylated γ-butyrolactones.

AB - Fluoride-catalyzed nucleophilic trifluoromethylation of acid anhydrides using CF3SiMe3 provided the corresponding γ-hydroxy-γ- trifluoromethyl-γ-butyrolactones. The utility of these adducts was further demonstrated by treatment with Grignard reagents, leading to γ-trifluoromethylated γ-butyrolactones.

KW - Anhydrides

KW - Ruppert-Prakash reagent

KW - Trifluoromethylation

KW - γ-Butyrolactones

UR - https://www.scopus.com/pages/publications/84885928593

U2 - 10.1016/j.jfluchem.2013.06.006

DO - 10.1016/j.jfluchem.2013.06.006

M3 - Article

AN - SCOPUS:84885928593

SN - 0022-1139

VL - 154

SP - 37

EP - 42

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

ER -

Nucleophilic trifluoromethylation of anhydrides employing (trifluoromethyl)trimethylsilane: Synthesis of γ-trifluoromethylated γ-butyrolactones

Abstract

Keywords

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