福山还原反应

Fukuyama还原反应(福山还原反应,Fukuyama reduction),由日本化学家福山透首先发现。

硫酯氢硅烷(silyl hydride)在催化量存在下还原,得到[1] 福山透最早所用的氢硅烷为三乙基硅烷,催化剂为钯碳



此反应用于将羧酸分步还原为醛。

反应机理

反应的催化循环如下:

R-C(O)-SR + pd(0) → RC(O)-Pd(II)-SR
  • 配体交换
RC(O)-Pd(II)-SR + R3SiH → RC(O)-Pd(II)-H + R3Si-SR
RC(O)-Pd(II)-H → RC(O)-H + Pd(0)

拓展

从 SMe-取代物合成BODIPY核心结构:[2](所用试剂为噻吩-2-甲酸亚铜(CuTC)、三(二亚苄基丙酮)二钯三(2-呋喃基)膦


参见

参考资料

  1. Facile reduction of ethyl thiol esters to aldehydes: application to a total synthesis of (+)-neothramycin A methyl ether Tohru Fukuyama, Shao Cheng Lin, Leping Li J. Am. Chem. Soc., 1990, 112 (19), pp 7050–7051 doi:10.1021/ja00175a043
  2. The Smallest and One of the Brightest. Efficient Preparation and Optical Description of the Parent Borondipyrromethene System. I. J. Arroyo, R. Hu, G. Merino, B. Z. Tang, E. Peña-Cabrera, J. Org. Chem. 2009, ASAP
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