Journal of the American Chemical Society
Communication
amount of iron/diphosphine used (1 equiv, 88% D; 0.75 equiv,
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7
3% D; 0.5 equiv, 45% D, 0 equiv, 0% D; see Table S6),
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strongly suggesting that A is a species containing an iron atom.
Reaction of preformed A with allyl phenyl ether gave 2 in 54%
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In conclusion, we have found that iron-catalyzed directed
ortho-allylation proceeds smoothly to afford allylbenzene
derivatives with high γ selectivity and without isomerization
of the double bond to styrene derivatives. The reaction
demonstrates, for the first time, that iron-catalyzed directed C−
H bond activation could be utilized for coupling with an
electrophile. Further studies on iron-catalyzed coupling of C−
H bonds with electrophiles are ongoing.
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ASSOCIATED CONTENT
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*
S
Supporting Information
Experimental procedures and physical properties of the
AUTHOR INFORMATION
̈
(13) (a) Klein, H.-F.; Camadanli, S.; Beck, R.; Leukel, D.; Florke, U.
Angew. Chem., Int. Ed. 2005, 44, 975−977. (b) Beck, R.; Sun, H.; Li,
X.; Camadanli, S.; Klien, H.-F. Eur. J. Inorg. Chem. 2008, 3253−3257.
Notes
(
̈
c) Beck, R.; Zheng, T.; Sun, H.; Li, X.; Florke, U.; Klien, H.-F. J.
The authors declare no competing financial interest.
Organomet. Chem. 2008, 693, 3471−3478. (d) Camadanli, S.; Beck, R.;
Flo
̈
rke, U.; Klein, H.-F. Organometallics 2009, 28, 2300−2310.
ACKNOWLEDGMENTS
(14) Ilies, L.; Okabe, J.; Yoshikai, N.; Nakamura, E. Org. Lett. 2010,
2, 2838−2840.
■
1
We thank MEXT for financial support (KAKENHI Specially
Promoted Research No. 22000008 to E.N., Grant-in-Aid for
Young Scientists (B) No. 23750100 and Grant-in-Aid for
Scientific Research on Innovative Areas No. 25105711 to L.I.).
S.A. thanks the Japan Society for the Promotion of Science for
Young Scientists for a Research Fellowship (No. 23-8207).
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27, 1075−1089. (c) Nakamura, M.; Matsuo, K.; Inoue, T.;
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