Ueno Satoshi, Chatani Naoto, Kakiuchi Fumitoshi
Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
J Org Chem. 2007 Apr 27;72(9):3600-2. doi: 10.1021/jo070182g. Epub 2007 Apr 4.
The ruthenium-catalyzed alkenylation of C-H bonds with alkenylboronates has been explored for a series of aromatic ketones. The coupling reaction of pivalophenone (1) with 2-isopropenyl-5,5-dimethyl[1,3,2]dioxaborinane (2) gave the corresponding isopropenylation product in 73% yield. In the case of the reaction of a sterically congested alkenylboronate, such as 2-methylpropenylboronate (8), the yield was decreased slightly. When beta-styrylboronates were used, the corresponding coupling products were obtained in good yields. The reaction of acetophenone with alpha-styrylboronate afforded the corresponding 1:1 coupling product, exclusively.
针对一系列芳香酮，研究了钌催化的碳氢键与烯基硼酸酯的烯基化反应。新戊基苯乙酮（1）与2-异丙烯基-5,5-二甲基[1,3,2]二氧硼戊环（2）的偶联反应以73%的产率得到了相应的异丙烯基化产物。对于空间位阻较大的烯基硼酸酯，如2-甲基丙烯基硼酸酯（8），反应产率略有降低。当使用β-苯乙烯基硼酸酯时，能以良好的产率得到相应的偶联产物。苯乙酮与α-苯乙烯基硼酸酯的反应仅得到相应的1:1偶联产物。
