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

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• 作者：Yoshinari Sawama ; Kyoshiro Shibata ; Yuka Sawama ; Masato Takubo ; Yasunari Monguchi ; Norbert Krause ; Hironao Sajiki
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：October 18, 2013
• 年：2013
• 卷：15
• 期：20
• 页码：5282-5285
• 全文大小：254K
• 年卷期：v.15,no.20(October 18, 2013)
• ISSN：1523-7052

文摘

We have established the first catalytic C鈥揅 and C鈥揘 bond formation reactions of O-heterocycles (e.g., tetrahydrofuran, phthalane, and lactone derivatives) using iron trichloride as a catalyst in the presence of TMSN₃ or allylsilanes accompanied by the ring opening of O-heterocycles. The reactions smoothly proceeded at room temperature to give the corresponding primary saturated alcohols from the 2-substituted tetrahydrofurans, ortho-substituted benzyl alcohols from phthalanes, and saturated carboxylic acids from lactones in high yields.