Regioselective alkenylation of aromatic ketones with alkenylboronates using a RuH2(CO)(PPh3)3 catalyst via carbon-hydrogen bond cleavage.
Regioselective alkenylation of aromatic ketones with alkenylboronates using a RuH2(CO)(PPh3)3 catalyst via carbon-hydrogen bond cleavage.
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DOI：
10.1021/jo070182g
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发表时间：
2007-04
期刊：
影响因子：
--
通讯作者：
S. Ueno;N. Chatani;F. Kakiuchi
中科院分区：
文献类型：
--
作者：
S. Ueno;N. Chatani;F. Kakiuchi
研究了烯基硼酸盐催化的C-H键烯基化反应。新戊酮（1）与2-异丙烯基-5，5-二甲基[1，3，2]二氧杂硼杂环己烷（2）发生偶联反应，得到相应的异丙烯基化产物，产率为73%。在空间拥挤的烯基硼酸酯，如2-甲基丙烯基硼酸酯（8）的反应的情况下，产率略有下降。当使用β-苯乙烯基硼酸酯时，以良好的产率获得相应的偶联产物。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。
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.