10.1002/adsc.201700981
Advanced Synthesis & Catalysis
ethanol (0.22 mL), and water (0.22 mL) was added
bromoaldehyde 10 (120.8 mg, 0.53 mmol, 1.0 equiv.), and the
resulting mixture was stirred under nitrogen for 15min. Then
Pd(PPh3)4 (15.0 mg, 0.013 mmol, 2.5 mol %) was added in one
portion and the reaction mixture was slowly heated to reflux
under a steady stream of nitrogen. After the completion of the
reaction monitored by TLC, the reaction mixture was cooled to
ambient temperature and diluted with ether (9.0 mL) and filtered.
The resulting solution was concentrated under reduced pressure
and the crude product was purified by silica gel column
chromatography to provide pure coupled product 12 (90.0 mg,
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75
% yield). NOE interaction wasused to confirm the
configuration of product 12. The Z/E ratio(100/0) of product 12
was determined by 19F NMR analysis of the crude product.
(E)-3-Fluoro-2,3-diphenylacrylaldehyde (12): Pale yellow solid;
o
Melting point: 82-83 C;1H NMR(500 MHz, CDCl3): δ 10.51 (s,
1H), 7.38-7.34 (m, 4H), 7.31 (d, J = 7.5 Hz, 2H), 7.25 (t, J = 7.5
Hz, 2H), 7.13 (dd, J1 = 6.5 Hz, J2 = 3.0 Hz, 2H);13C NMR (125
MHz, CDCl3): δ 189.0 (d, J = 17.13 Hz), 169.6 (d, J = 272.38
Hz), 131.4, 131.0 (d, J = 5.38 Hz), 130.6 (d, J = 2.63 Hz), 130.1
(d, J = 26.5 Hz), 129.0 (d, J = 8.0 Hz), 128.8, 128.4, 128.3 (d, J =
4.0 Hz), 123.2 (d, J = 27.5 Hz); 19F NMR (470 MHz, CDCl3): δ -
102.74 (s, 1F); IR (neat): ν 3064, 2896, 2777, 1671, 1626, 1597,
1494, 1444, 1405, 1334, 1229, 1128, 1011, 776, 721, 692, 652,
606 cm-1; HRMS(ESI): calculated for C15H11FNaO [M+Na]+
249.0686, found 249.0689.
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Acknowledgements
We gratefully acknowledge the financial support from the
National Natural Science Foundation of China (No. 21404083,
51533007, 21472053 and 81502427), the China National Funds
for Distinguished Young Scientists (51325302), and the Wuhan
University of Technology fund for first-class university and first-
class discipline construction projects (472-20162008). The
Fundamental Research Funds for the Central Universities
(WUT2016IB006 and WUT 2017IB006) and the Natural Science
Foundation of Hubei Province (No. 2016CFB338) are also
acknowledged.
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