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Iron-Catalyzed Ring-Opening Azidation and Allylation of O-Heterocycles

Yoshinari Sawama*, Kyoshiro Shibata, Yuka Sawama, Masato Takubo, Yasunari Monguchi, Norbert Krause and Hironao Sajiki*

*Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan, Email:,

Y. Sawama, K. Shibata, Y. Sawama, M. Takubo, Y. Monguchi, N. Krause, H. Sajiki, Org. Lett., 2013, 15, 5282-5285.

DOI: 10.1021/ol402511r (free Supporting Information)

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A catalytic amount of iron trichloride enables C-C and C-N bond formation reactions of O-heterocycles accompanied by ring opening in the presence of TMSN3 or allylsilanes. The reactions smoothly proceeded at room temperature to give the corresponding primary saturated alcohols from 2-substituted tetrahydrofurans, ortho-substituted benzyl alcohols from phthalanes, and saturated carboxylic acids from lactones in high yields.

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Key Words

benzyl azides, allyl azides

ID: J54-Y2013