10.1002/chem.201802003
Chemistry - A European Journal
FULL PAPER
solution of tetrabutylammonium fluoride 1M in THF was added dropwise
at room temperature. The solution was stirred overnight at room
temperature. The solvent was evaporated and the crude was solved in
ethyl acetate (50 mL) and H2O (50 mL) was added. The mixture was
extracted with ethyl acetate ((3 × 50 mL) and the organic layers were dried
with Na2SO4. Pure product (C, 360 mg, 1.55 mmol) was isolated in pure
form by column chromatography (Si-gel, n-Hexane : Ethyl Acetate = 9:1).
Yield 99 %. 1H NMR (CDCl3; 400 MHz) d1.54 (9H, s); 3.06 (1H, s); 6.51
(1H, s); 7.18 (1H, d, J = 7.8 Hz); 7.25 (1H, t, J = 7.8 Hz); 7.37 (1H, d, J =
7.4 Hz); 7.55 (1H, s) (see supplementary figure 5)
Keywords: Ethynylaniline, resonating structures, thermal
hydrosilylation, nucleophilic addition
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Conflicts of interest
The authors declared no conflict of interest in this work
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Author’s Contributions
Both Joline Tung and Lih Shin Tew had contributed equally in this
work and had performed the thermal hydrosilylation as well as the
XPS measurements. Dr. Carmine Coluccini had assisted in the
synthesis of the amino Boc-protected derivatives while Professor Yue-
Der Lin had provided the necessary AFM measurements. Dr. Yit Lung
Khung had conceived the project concept as well as having written
this manuscript.
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Acknowledgements
The work was carried out with assistance from university grant
(CMU-1055918D) and grant under Ministry of Science and
Technology in Taiwan (MOST 105-2218-E-039-002 and MOST
106-2221-E-035-024-MY2).
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