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G. W. Kabalka et al. / Tetrahedron Letters 42 (2001) 6239–6241
6241
11H); 13C NMR l 164.2, 160.3, 136.8, 129.3, 129.1,
115.4, 115.0, 68.9, 45.8, 30.2, 26.1, 25.0. Anal. calcd for
C13H16CIF: C, 68.87; H, 7.11. Found: C, 68.66; H, 7.14.
14. Batey, R. A.; Mackay, D. B.; Santhakumar, V. J. Am.
Chem. Soc. 1999, 121, 5075.
15. Brown, H. C.; Knights, E. F.; Scouten, C. G. J. Am.
Chem. Soc. 1974, 96, 7765.
In summary, the new alkylation reaction provides a
potentially useful alternative to traditional alkylation
reactions. The reaction occurs under mild conditions
and affords arylalkyl chlorides in good yields. The
reaction is limited to aldehydes which do not possess
a-hydrogens due to the well-known enolization reac-
tions that occur with boron halides.
16. (a) Mikhailov, B. M.; Kiselev, V. G.; Bubnov, Y. N. Bull.
Acad. Sci. USSR, Div. Chem. Sci. 1965, 865; (b)
Mikhailov, B. M.; Bubnov, Y. N.; Kiselev, V. G. J. Gen.
Chem. USSR 1966, 36, 65.
17. (a) Kabalka, G. W.; Maddox, J. T.; Bogas, E.; Kelly, S.
W. J. Org. Chem. 1997, 62, 3688; (b) Okada, K.; Hosoda,
Y.; Oda, M. Tetrahedron Lett. 1986, 6213.
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Acknowledgements
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Mukaiyama, T.; Soai, K.; Sato, T.; Shimmizu, H.;
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We wish to thank the US Department of Energy and
the Robert H. Cole Foundation for support of this
research.
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