A reverse Wittig coupling with trifluoroacetaldehyde: A convenient one-step synthesis of trifluoromethyl alkenes

Shainaz M. Landge; Dmitry A. Borkin; Béla Török

doi:10.2174/157017809789124795

A reverse Wittig coupling with trifluoroacetaldehyde: A convenient one-step synthesis of trifluoromethyl alkenes

Shainaz M. Landge
, Dmitry A. Borkin
, Béla Török

Biochemistry, Chemistry & Physics

University of Massachusetts Boston

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

12 Scopus citations

Abstract

A novel, mild synthesis of aryl-3,3,3-trifluoropropenes by Wittig olefmation of benzylphosphonium ylides with in-situ generated trifluoroacetaldehyde is described. The in-situ formed trifluoroacetaldehyde efficiently traps the Wittig ylides and yields trifluoromethyl alkenes without the troublesome handling. The scope of the reaction was tested in reaction of trifluoroacetaldehyde with a wide variety of benzylphosphonium ylides. The α-trifluoromethyl alkenes were isolated in good to excellent yields in a convenient one step process.

Original language	English
Pages (from-to)	439-443
Number of pages	5
Journal	Letters in Organic Chemistry
Volume	6
Issue number	6
DOIs	https://doi.org/10.2174/157017809789124795
State	Published - Sep 2009

Scopus Subject Areas

Biochemistry
Organic Chemistry

Disciplines

Chemistry

Keywords

Aryl-α-trifluoromethyl-alkenes
Fluoral
Trifluoroacetaldehyde ethyl hemiacetal
Witting coupling

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10.2174/157017809789124795

Cite this

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title = "A reverse Wittig coupling with trifluoroacetaldehyde: A convenient one-step synthesis of trifluoromethyl alkenes",

abstract = "A novel, mild synthesis of aryl-3,3,3-trifluoropropenes by Wittig olefmation of benzylphosphonium ylides with in-situ generated trifluoroacetaldehyde is described. The in-situ formed trifluoroacetaldehyde efficiently traps the Wittig ylides and yields trifluoromethyl alkenes without the troublesome handling. The scope of the reaction was tested in reaction of trifluoroacetaldehyde with a wide variety of benzylphosphonium ylides. The α-trifluoromethyl alkenes were isolated in good to excellent yields in a convenient one step process.",

keywords = "Aryl-α-trifluoromethyl-alkenes, Fluoral, Trifluoroacetaldehyde ethyl hemiacetal, Witting coupling",

author = "Landge, \{Shainaz M.\} and Borkin, \{Dmitry A.\} and B{\'e}la T{\"o}r{\"o}k",

note = "Shainaz M. Landge, Dmitry A. Borkin, and B{\'e}la T{\"o}r{\"o}k. {"}A Reverse Wittig Coupling with Trifluoroacetaldehyde: A convenient one-step synthesis of Trifluoromethyl Alkenes{"} The Journal of Organic Chemistry 6.6 (2009): 439-443. doi:10.2174/157017809789124795",

year = "2009",

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doi = "10.2174/157017809789124795",

language = "English",

volume = "6",

pages = "439--443",

journal = "Letters in Organic Chemistry",

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TY - JOUR

T1 - A reverse Wittig coupling with trifluoroacetaldehyde

T2 - A convenient one-step synthesis of trifluoromethyl alkenes

AU - Landge, Shainaz M.

AU - Borkin, Dmitry A.

AU - Török, Béla

N1 - Shainaz M. Landge, Dmitry A. Borkin, and Béla Török. "A Reverse Wittig Coupling with Trifluoroacetaldehyde: A convenient one-step synthesis of Trifluoromethyl Alkenes" The Journal of Organic Chemistry 6.6 (2009): 439-443. doi:10.2174/157017809789124795

PY - 2009/9

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N2 - A novel, mild synthesis of aryl-3,3,3-trifluoropropenes by Wittig olefmation of benzylphosphonium ylides with in-situ generated trifluoroacetaldehyde is described. The in-situ formed trifluoroacetaldehyde efficiently traps the Wittig ylides and yields trifluoromethyl alkenes without the troublesome handling. The scope of the reaction was tested in reaction of trifluoroacetaldehyde with a wide variety of benzylphosphonium ylides. The α-trifluoromethyl alkenes were isolated in good to excellent yields in a convenient one step process.

AB - A novel, mild synthesis of aryl-3,3,3-trifluoropropenes by Wittig olefmation of benzylphosphonium ylides with in-situ generated trifluoroacetaldehyde is described. The in-situ formed trifluoroacetaldehyde efficiently traps the Wittig ylides and yields trifluoromethyl alkenes without the troublesome handling. The scope of the reaction was tested in reaction of trifluoroacetaldehyde with a wide variety of benzylphosphonium ylides. The α-trifluoromethyl alkenes were isolated in good to excellent yields in a convenient one step process.

KW - Aryl-α-trifluoromethyl-alkenes

KW - Fluoral

KW - Trifluoroacetaldehyde ethyl hemiacetal

KW - Witting coupling

UR - https://www.scopus.com/pages/publications/70349291332

U2 - 10.2174/157017809789124795

DO - 10.2174/157017809789124795

M3 - Article

SN - 1570-1786

VL - 6

SP - 439

EP - 443

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

IS - 6

ER -

A reverse Wittig coupling with trifluoroacetaldehyde: A convenient one-step synthesis of trifluoromethyl alkenes

Abstract

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Keywords

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