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Journal of the American Chemical Society
S.; Linden, A.; Cavallo, L.; Dorta, R. Angew. Chem., Int. Ed. 2012, 51, 2870;
(i) Mei, H. B.; Xie, C.; Acena, J. L.; Soloshonok, V. A.; Roschenthaler, G.
V.; Han, J. Eur. J. Org. Chem. 2015, 6401.
The authors declare no competing financial interest.
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ACKNOWLEDGMENT
(8) (a) Reddy, D. S.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.;
Kanemasa, S. Angew. Chem., Int. Ed. 2008, 47, 164; (b) Han, X.;
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Jiang, Z. Y.; Tan, C. H. Chem. Eur. J. 2010, 16, 779; (d) Yoon, S. J.; Kang, Y.
K.; Kim, D. Y. Synlett 2011, 420.
(9) (a) Yang, X. Y.; Phipps, R. J.; Toste, F. D. J. Am. Chem. Soc. 2014,
136, 5225; (b) Liang, Y. F.; Fu, G. C. J. Am. Chem. Soc. 2014, 136, 5520.
(10) (a) Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541; (b)
Guo, Y.; Twamley, B.; Shreeve, J. M. Org. Biomol. Chem. 2009, 7, 1716; (c)
Guo, Y.; Tao, G. H.; Blumenfeld, A.; Shreeve, J. M. Organometallics 2010,
29, 1818; (d) Guo, C.; Wang, R. W.; Guo, Y.; Qing, F. L. J. Fluorine Chem.
2012, 133, 86.
We thank the Singapore Ministry of Education Academic Rese-
arch Fund (MOE2013-T2-2-057, MOE2014-T1-001-021), the
NIH (GM58108, F32GM106641), and the NSF (CHE-
1565886) for financial support. We thank Yicheng Weng for
preliminary data on the reactions of fluorinated ketones.
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(21) We also generated the sodium enolate of tetralone 5 by direct
deprotonation with NaOt-Bu, and by elimination of trifluoroacetate from
adduct 7a in the presence of NaOt-Bu. Both methods for forming this
enolate generate species that have identical 1H-, 13C- and 19F-NMR
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coupled products. We do not yet understand the origin of this difference.
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