RhI-Catalyzed Two-Component [(5+2)+1] Cycloaddition Approach toward [5-8-5] Ring Systems
RhI-Catalyzed Two-Component [(5+2)+1] Cycloaddition Approach toward [5-8-5] Ring Systems
复制标题
DOI：
10.1002/asia.201000053
复制
发表时间：
2010-01-01
影响因子：
4.1
通讯作者：
Yu, Zhi-Xiang
中科院分区：
文献类型：
--
作者：
Huang, Feng;Yao, Zhong-Ke;Yu, Zhi-Xiang
除非另有说明，空气和湿气敏感反应在干燥的CO混合气体或来自气球的氮气的正压下，在用橡胶隔片密封的烘干玻璃器皿中进行。类似的敏感液体和溶液通过注射器转移。使用特氟隆涂层的磁力搅拌棒搅拌反应物。使用恒温器控制的硅油浴维持升高的温度。使用带有台式真空泵的 Büchi 旋转蒸发器浓缩有机溶液。四氢呋喃和乙醚在使用前从钠和二苯甲酮中蒸馏出来。二恶烷（超干，水< 50 ppm），[Rh (CO) 2Cl] 2 可商购并按收到时的状态使用。使用具有 254 nm 荧光指示剂的 0.25 mm 硅胶 60F 板进行分析 TLC。通过紫外光并用酸性对茴香醛染色剂处理然后温和加热来使TLC板可视化。通过硅胶快速色谱法完成产物的纯化，并且纯化的化合物通过分析TLC显示单点。 NMR 谱在 Varian INOVA 600（600 MHz 下 1H，150 MHz 下 13C）磁共振波谱仪上测量。 1H-NMR谱的数据报告如下：化学位移（ppm：s=单峰、d=双峰、t=三重峰、q=四重峰、dd=双峰的双峰、td=双峰的三重峰、ddd=双峰的双峰、tdd=双峰的三重峰、m=多重峰）、耦合常数（Hz）和积分。 13C-NMR 数据以相对于残留溶剂峰的化学位移 (ppm) 形式报告。红外光谱在 AVATAR 330 傅里叶变换光谱仪 (FT-IR) 上记录，并以波数 (cm-1) 报告。质谱 (MS) 和高分辨率质谱 (HRMS) 在 VG-ZAB-HS 质谱仪 (EI, 70 eV) 上记录。缩写： THF= 四氢呋喃 PE= 石油醚 EA= 乙酸乙酯 DCE= 1, 2-二氯乙烷 PCC：氯铬酸吡啶 PDC：重铬酸吡啶 DIBAL-H: 二异丁基氢化铝 DEAD= 偶氮二甲酸二乙酯 mp= 熔点
Air and moisture sensitive reactions were carried out in oven-dried glassware sealed with rubber septa under a positive pressure of dry CO mixed gas or nitrogen from a balloon, unless otherwise indicated. Similarly sensitive liquids and solutions were transferred via syringe. Reactions were stirred using Teflon-coated magnetic stir bars. Elevated temperatures were maintained using thermostat-controlled silicone oil baths. Organic solutions were concentrated using a Büchi rotary evaporator with a desktop vacuum pump. Tetrahydrofuran and diethyl ether were distilled from sodium and benzophenone prior to use. Dioxane (extra dry, water< 50 ppm),[Rh (CO) 2Cl] 2 was commercially available and used as received. Analytical TLC was performed with 0.25 mm silica gel 60F plates with a 254 nm fluorescent indicator. The TLC plates were visualized by ultraviolet light and treatment with acidic p-anisaldehyde stain followed by gentle heating. Purification of products was accomplished by flash chromatography on silica gel and the purified compounds show a single spot by analytical TLC. NMR spectra were measured on a Varian INOVA 600 (1H at 600 MHz, 13C at 150 MHz) magnetic resonance spectrometer. Data for 1H-NMR spectra are reported as follows: chemical shift (ppm: s= singlet, d= doublet, t= triplet, q= quartet, dd= doublet of doublets, td= triplet of doublets, ddd= doublet of doublet of doublets, tdd= triplet of doublet of doublets, m= multiplet), coupling constant (Hz), and integration. Data for 13C-NMR are reported in terms of chemical shift (ppm) relative to residual solvent peak. Infrared spectra were recorded on an AVATAR 330 Fourier transform spectrometer (FT-IR) and are reported in wavenumbers (cm-1). Mass spectra (MS) and high-resolution mass spectra (HRMS) were recorded on a VG-ZAB-HS mass spectrometer (EI, 70 eV).Abbreviations: THF= tetrehydrofuran PE= petroleum ether EA= ethyl acetate DCE= 1, 2-dichloroethane PCC: Pyridinium Chlorochromate PDC: Pyridinium Dichromate DIBAL-H: Diisobutylaluminum Hydride DEAD= diethyl azodicarboxylate mp= melting point