Deoxygenative Allylation of Benzyl Acetates and Cinnamyl Alcohols Catalyzed by Molecular Iodine
作者:J. S. Yadav、B. V. Subba Reddy、A. Srinivas Reddy、B. Eeshwaraiah
DOI:10.1246/cl.2007.1500
日期:2007.12.5
Benzyl acetates undergo smooth deoxygenative allylation with allyltrimethylsilane in the presence of 10 mol % of molecular iodine under mild conditions to afford the corresponding allyl derivatives in excellent yields and with high selectivity. Cinnamyl alcohols also react readily with allylsilane under similar conditions. The use of molecular iodine makes this method quite simple, more convenient
condition using cetyltrimithylammonium bromide (CTAB) as surfactant. This solid was characterized using several techniques e.g. powder X-ray diffraction (XRD), N2 adsorption-desorption, FT-IR, TG/DTG and pyridine adsorption-desorption followed by IR spectroscopy. The catalytic performance of Al-MCM-41 catalyst as Lewis acid was used without treatment and was compared with TiCl4 in the allylation of aromatic
摘要 以十六烷基三甲基溴化铵(CTAB)为表面活性剂,在水热条件下合成了Si/Al比为12.5的介孔Al-MCM-41分子筛。使用几种技术表征该固体,例如粉末 X 射线衍射 (XRD)、N2 吸附-解吸、FT-IR、TG/DTG 和吡啶吸附-解吸,然后是红外光谱。Al-MCM-41 催化剂作为路易斯酸的催化性能在未经处理的情况下使用,并与 TiCl4 在芳族醛与烯丙基三甲基硅烷的烯丙基化反应中进行了比较。结果表明,在 Al-MCM-41 的存在下,无论芳香醛的性质如何,在 35 °C 的温度下都获得高烯丙基甲硅烷基醚。当使用 TiCl4 时,反应需要 -85 °C 的温度,并且获得的所有产物都是由于二烯丙基化。为了解释在 Al-MCM-41 或 TiCl4 存在下这种不同的烯丙基化,提出了两种可能的反应机制。Al-MCM-41 用于连续四次实验,没有明显的活性损失,证实了它的稳定性。最后,
Preparation of 4‐Arylcyclopentenes by Sequential Diallylation of Arylaldehydes and Ring‐Closing Metathesis