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3 protocols using trifluorobenzene

1

Fluorinated Benzene Compounds Evaluation

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The following standards/reagents were purchased from Sigma Aldrich at 99 % purity: Anisole and the fluorinated benzenes fluorobenzene (FB), 1,2-difluorobenzene (12DFB), 1,3-difluorobenzene (13DFB), 1,4-difluorobenzene (14DFB), 1,2,3-trifluorobenzene (123TFB), 1,2,4-trifluorobenzene (124TFB), 1,3,5-trifluorobenzene (135TFB), 1,2,3,4-tetrafluoro-benzene (1234TFB), 1,2,3,5-tetrafluoro-benzene (1235TFB), 1,2,4,5-tetrafluorobenzene (1245TFB), pentafluorobenzene (PFB) and hexafluorobenzene (HFB). Also, the solvents hexane, acetonitrile and isopropyl alcohol and the proteins l-tyrosine (l-Tyr), phenylalanine (Phe) and pentafluorophenylalanine (F5Phe) are purchased from Sigma Aldrich. Deionized water was obtained from a Millipore Q-POD water deionizer and purifier.
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2

Fluorinated Benzene Compounds Evaluation

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The following standards/reagents were purchased from Sigma Aldrich at 99 % purity: Anisole and the fluorinated benzenes fluorobenzene (FB), 1,2-difluorobenzene (12DFB), 1,3-difluorobenzene (13DFB), 1,4-difluorobenzene (14DFB), 1,2,3-trifluorobenzene (123TFB), 1,2,4-trifluorobenzene (124TFB), 1,3,5-trifluorobenzene (135TFB), 1,2,3,4-tetrafluoro-benzene (1234TFB), 1,2,3,5-tetrafluoro-benzene (1235TFB), 1,2,4,5-tetrafluorobenzene (1245TFB), pentafluorobenzene (PFB) and hexafluorobenzene (HFB). Also, the solvents hexane, acetonitrile and isopropyl alcohol and the proteins l-tyrosine (l-Tyr), phenylalanine (Phe) and pentafluorophenylalanine (F5Phe) are purchased from Sigma Aldrich. Deionized water was obtained from a Millipore Q-POD water deionizer and purifier.
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3

Synthesis of Fluorinated Benzene Derivatives

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Unless stated
otherwise, all
reactions were carried out in air. Solvents were distilled and dried
as required. Pentafluorobenzene, 1,2,4,5-tetrafluorobenzene, 1,3,5-trifluorobenzene,
sodium tert-butoxide, diethyl malonate, trimethylsilyl
cyanide, triethoxysilane, triflimide, tert-butyl
alcohol, tBuNC, KCN, and norbornene were
purchased from Sigma-Aldrich and used as received. (AdCAAC)AuCl6c and Me2CAAC47 were obtained according to a literature procedure. 1H, 13C{1H}, and 19F NMR spectra were recorded
using a Bruker Avance DPX-300 MHz NMR spectrometer. 1H
NMR spectra (300.13 MHz) and 13C{1H} (75.47
MHz) were referenced to CD2Cl2 at δ 5.32
(13C, δ 54.0), C6D6 at δ
7.16 (13C, δ 128.4), CDCl3 at δ
7.26 (δ 13C 77.2), or C6D5Br
at δ 7.30 for the most downfield signal (13C, δ
122.5 for the most upfield signal) ppm. 19F NMR spectra
(282.4 MHz) were referenced externally to CFCl3 and internally
to C6F6F −164.9).
IR spectra were recorded using a PerkinElmer Spectrum One FT-IR spectrometer
equipped with a diamond ATR attachment. Elemental analyses were performed
by the London Metropolitan University.
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