Laboratory of Organic Chemistry, Gifu Pharmaceutical University , 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan, Laboratory of Pharmaceutical Physical Chemistry, Gifu Pharmaceutical University , 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan, and Organic Chemistry, Dortmund University of Technology , Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany.
Org Lett. 2013 Oct 18;15(20):5282-5. doi: 10.1021/ol402511r. Epub 2013 Oct 1.
We have established the first catalytic C-C and C-N 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.
我们已经利用三氯化铁作为催化剂，在 TMSN3 或烯丙基硅烷的存在下，实现了 O-杂环（如四氢呋喃、邻苯二甲烷和内酯衍生物）的首例催化 C-C 和 C-N 键形成反应，同时伴随着 O-杂环的开环。这些反应在室温下顺利进行，从 2-取代的四氢呋喃中得到相应的仲饱和醇，从邻苯二甲烷中得到邻位取代的苄醇，从内酯中得到饱和羧酸，产率很高。
