Shi Lei, Tu Yong-Qiang, Wang Min, Zhang Fu-Min, Fan Chun-An, Zhao Yu-Ming, Xia Wu-Jiong
State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
J Am Chem Soc. 2005 Aug 10;127(31):10836-7. doi: 10.1021/ja0528331.
A new method for intermolecular sp3-sp3 C-C bond formation between primary aliphatic alcohol and olefin by use of a RhCl(PPh3)3 (cat.)/BF3.OEt2 (2.5 equiv)/BuBr (0.5 equiv)/toluene system was first disclosed, which possessed quite significant utilities for organic synthesis, especially for that of secondary alcohols. The most significant aspect is the discovery that rhodium-catalyzed C-H bond activation of alcohols is feasible under Lewis acid-promoted conditions.
首次公开了一种使用RhCl(PPh3)3(催化剂)/BF3·OEt2(2.5当量)/BuBr(0.5当量)/甲苯体系在伯脂肪醇和烯烃之间形成分子间sp3-sp3 C-C键的新方法,该方法在有机合成中具有相当重要的用途,特别是对于仲醇的合成。最显著的方面是发现铑催化的醇的C-H键活化在路易斯酸促进的条件下是可行的。