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metal catalysts for C−H functionalization, the present method
provides unique synthetic examples for the utilization of an
alcohol and the corresponding tosylate and mesylate as an
electrophile. Another feature of the reaction is the lack of
regioisomerization in the reaction of a secondary tosylate and the
lack of stereoisomerization of olefins in the product. Although
the interest in iron catalysis18,19 has so far been driven largely by
its economic and environmental merits,20 the present results
suggest that iron catalysis may become more synthetically
versatile than precious metal catalysis.21
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4309.
ASSOCIATED CONTENT
■
S
* Supporting Information
Experimental procedures and physical properties of the
compounds. This material is available free of charge via the
AUTHOR INFORMATION
■
Corresponding Authors
Present Address
†Division of Chemistry and Biotechnology, Graduate School of
Natural Science and Technology, Okayama University, 3-1-1
Tsushimanaka, Kita-ku, Okayama 700-8530, Japan.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
(14) (a) Cahiez, G.; Chaboche, C.; Mahuteau-Betzer, F.; Ahr, M. Org.
Lett. 2005, 7, 1943−1946. (b) Nagano, T.; Hayashi, T. Org. Lett. 2005, 7,
491−493.
■
We thank MEXT for financial support (KAKENHI No.
22000008 to E.N. and Grant-in-Aid for Scientific Research on
Innovative Areas No. 25105711 and Grant-in-Aid for Young
Scientists (A) No. 26708011 for to L.I.). T.M. and S.A. thank the
Japan Society for the Promotion of Science for Young Scientists
for a Research Fellowship (No. 26-11422 and No. 23-8207,
respectively). T.M. was supported by the Japan Society for the
Promotion of Science through Program for Leading Graduate
Schools (MERIT).
(15) (a) Norinder, J.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. J.
Am. Chem. Soc. 2008, 130, 5858−5859. (b) Yoshikai, N.; Matsumoto,
A.; Norinder, J.; Nakamura, E. Angew. Chem., Int. Ed. 2009, 48, 2925−
2928. (c) Yoshikai, N.; Asako, S.; Yamakawa, T.; Ilies, L.; Nakamura, E.
Chem.Asian J. 2011, 6, 3059−3065. (d) Ilies, L.; Konno, E.; Chen, Q.;
Nakamura, E. Asian J. Org. Chem. 2012, 1, 142−145.
(16) Do, H.-Q.; Chandrashekar, E. R. R.; Fu, G. C. J. Am. Chem. Soc.
2013, 135, 16288−16291.
(17) We thank a reviewer for suggesting this reaction to us.
(18) Selected reviews: (a) Bolm, C.; Legros, J.; Le Paih, J.; Zani, L.
Chem. Rev. 2004, 104, 6217−6254. (b) Plietker, B., Ed.; Iron Catalysis in
Organic Chemistry; Wiley-VCH: Weinheim, Germany, 2008. (c) En-
thaler, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2008, 47, 3317−
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