Journal of the American Chemical Society
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Scheme 4. Synthesis of Liquid-Crystalline Compound 17
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a
Reagents and conditions: (a) 2,2-dimethyl-1,3-propanediol, toluene,
reflux, 10 h; (b) [CuOtBu], Phen, TFE, THF, 40 °C, 5 h; (c) 4-
(CO2Et)C6H4I, THF, 60 °C, 4 h; (d) KOH, MeOH/H2O, 60 °C, 12
h; (e) H2, cat. Rh/Al, AcOH, 60 °C, 12 h; (f) 3,4,5-trifluorophenol,
DCC, DMAP, CH2Cl2, rt, 24 h.
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Shibata, M.; Ogoshi, S. Eur. J. Org. Chem. 2013, 443. (c) Ohashi, M.;
Kamura, R.; Doi, R.; Ogoshi, S. Chem. Lett. 2013, 42, 933. (d) Saijo, H.;
Sakaguchi, H.; Ohashi, M.; Ogoshi, S. Organometallics 2014, 33, 3669.
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ASSOCIATED CONTENT
* Supporting Information
Procedures and analytical and spectral data. This material is
■
S
AUTHOR INFORMATION
Corresponding Author
Notes
■
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was partially supported by a Grant-in-Aid for Scientific
Research (A) (21245028), a Grant-in-Aid for Young Scientist
(A) (25708018), and a Grant-in-Aid for Scientific Research on
Innovative Areas “Molecular Activation Directed toward
Straightforward Synthesis” (23105546) from MEXT and by
Adaptable and Seamless Technology Transfer Program through
target-driven R&D (A-STEP) (AS2525804M) from JST. We
express our thanks to Daikin Industries, Ltd., for supplying TFE.
M.O. also acknowledges The Noguchi Institute.
(14) Gatenyo, J.; Rozen, S. J. Fluorine Chem. 2009, 130, 332 and
references therein.
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9837 and references therein.
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(17) A few 1,4-addition reactions of organocuprates with fluorinated
enones had been reported, but no fluoroalkylcopper complex had been
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