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

9 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

Keywords

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

Access to Document

10.2174/157017809789124795

Cite this

@article{d7689554c26d4bdda539b8aa083e6d69,

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",

year = "2009",

month = sep,

doi = "10.2174/157017809789124795",

language = "English",

volume = "6",

pages = "439--443",

journal = "Letters in Organic Chemistry",

issn = "1570-1786",

publisher = "Bentham Science Publishers B.V.",

number = "6",

}

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

PY - 2009/9

Y1 - 2009/9

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 - http://www.scopus.com/inward/record.url?scp=70349291332&partnerID=8YFLogxK

U2 - 10.2174/157017809789124795

DO - 10.2174/157017809789124795

M3 - Article

AN - SCOPUS:70349291332

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

Keywords

Access to Document

Other files and links

Fingerprint

Cite this