Iron-Catalyzed Ring-Opening Azidation and Allylation of <i>O</i>‑Heterocycles
Yoshinari Sawama
Kyoshiro Shibata
Yuka Sawama
Masato Takubo
Yasunari Monguchi
Norbert Krause
Hironao Sajiki
10.1021/ol402511r.s001
https://acs.figshare.com/articles/journal_contribution/Iron_Catalyzed_Ring_Opening_Azidation_and_Allylation_of_i_O_i_Heterocycles/2365333
We have established the first catalytic C–C and C–N bond formation reactions of <i>O</i>-heterocycles (e.g., tetrahydrofuran, phthalane, and lactone derivatives) using iron trichloride as a catalyst in the presence of TMSN<sub>3</sub> or allylsilanes accompanied by the ring opening of <i>O</i>-heterocycles. The reactions smoothly proceeded at room temperature to give the corresponding primary saturated alcohols from the 2-substituted tetrahydrofurans, <i>ortho</i>-substituted benzyl alcohols from phthalanes, and saturated carboxylic acids from lactones in high yields.
2016-02-18 14:58:51
allylsilane
presence
carboxylic acids
phthalane
tetrahydrofuran
Azidation
Allylation
formation
catalyst
benzyl
iron trichloride
e.g
TMSN 3
yield
room temperature
lactone derivatives
ring opening
bond