Nickel/BPh3-catalyzed alkynylcyanation of alkynes and 1,2-dienes:: An efficient route to highly functionalized conjugated enynes
Nickel/BPh3-catalyzed alkynylcyanation of alkynes and 1,2-dienes:: An efficient route to highly functionalized conjugated enynes
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DOI：
10.1002/anie.200704095
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发表时间：
2008-01-01
影响因子：
16.6
通讯作者：
Hiyama, Tamejiro
中科院分区：
文献类型：
--
作者：
Nakao, Yoshiaki;Hirata, Yasuhiro;Hiyama, Tamejiro
一般的。对氧和湿气敏感材料的所有操作均采用标准 Schlenk 技术或在氩气气氛下的干燥箱中进行。使用关东化学硅胶（球形，40–50 µm）进行快速柱色谱。在 Merck Kieselgel 60 F254 (0.25 mm) 板上进行分析薄层色谱 (TLC)。使用紫外光(254 nm)和/或碱性KMnO 4 水溶液然后加热来完成可视化。设备。质子和碳核磁共振波谱（1H NMR 和 13C NMR）在 Varian Mercury 400（1H NMR，400 MHz；13C NMR，101 MHz）波谱仪上记录，以溶剂共振作为内标（1H NMR，CHCl3 为 7.26 ppm；13C NMR，CDCl3 为 77.0 ppm）。 1H NMR 数据报告如下：化学位移、多重性（s= 单峰、d= 双峰、t= 三重峰、q= 四重峰、quint= 五重峰、sext= 六重峰、br= 宽峰、m= 多重峰）、耦合常数 (Hz) 和积分。使用YANAKO MP-500D测定熔点。元素分析由京都大学元素分析中心进行。使用 JEOL JMS-700 (EI) 或 JEOL JMS-HX110A (FAB+) 光谱仪获得高分辨率质谱。使用配备 JAIGEL-1H 和-2H（氯仿作为洗脱剂）和 JAIGEL-SIL 或 Nacalai tesque 5SL-II（己烷-乙酸乙酯作为洗脱剂）的 JAI LC-908 色谱仪进行制备型回收凝胶渗透色谱（GPC）和制备型回收硅胶色谱。 GC分析在配备有ENV-1柱(Kanto Chemical，30 mx 0.25 mm，压力＝31.7 kPa，检测器＝FID，290℃)的Shimadzu GC 2014上以氦气作为载体进行。
General. All manipulations of oxygen-and moisture-sensitive materials were conducted with a standard Schlenk technique or in a dry box under an argon atmosphere. Flash column chromatography was performed using Kanto Chemical silica gel (spherical, 40–50 µm). Analytical thin layer chromatography (TLC) was performed on Merck Kieselgel 60 F254 (0.25 mm) plates. Visualization was accomplished with UV light (254 nm) and/or an aqueous alkaline KMnO4 solution followed by heating.Apparatus. Proton and carbon nuclear magnetic resonance spectra (1H NMR and 13C NMR) were recorded on a Varian Mercury 400 (1H NMR, 400 MHz; 13C NMR, 101 MHz) spectrometer with solvent resonance as the internal standard (1H NMR, CHCl3 at 7.26 ppm; 13C NMR, CDCl3 at 77.0 ppm). 1H NMR data are reported as follows: chemical shift, multiplicity (s= singlet, d= doublet, t= triplet, q= quartet, quint= quintet, sext= sextet, br= broad, m= multiplet), coupling constants (Hz), and integration. Melting points were determined using a YANAKO MP-500D. Elemental analyses were performed by Elemental Analysis Center of Kyoto University. High-resolution mass spectra were obtained with a JEOL JMS-700 (EI) or JEOL JMS-HX110A (FAB+) spectrometer. Preparative recycling gel permeation chromatography (GPC) and preparative recycling silica gel chromatography were performed with a JAI LC-908 chromatograph equipped with JAIGEL-1H and-2H (chloroform as an eluent) and JAIGEL-SIL or Nacalai tesque 5SL-II (hexane–ethyl acetate as an eluent). GC analysis was performed on a Shimadzu GC 2014 equipped with an ENV-1 column (Kanto Chemical, 30 mx 0.25 mm, pressure= 31.7 kPa, detector= FID, 290 C) with helium gas as a carrier.