159386-45-5Relevant academic research and scientific papers
Catalytic sp3C-CN Bond Cleavage: Ni-Mediated Phosphorylation of Alkylnitriles
Zhang, Ji-Shu,Chen, Tieqiao,Zhou, Yongbo,Yin, Shuang-Feng,Han, Li-Biao
, p. 6746 - 6749 (2018)
A direct phosphorylation of the sp3C-CN bond catalyzed by a nickel catalyst is disclosed. A wide range of primary nitriles readily coupled with secondary phosphine oxides to produce the corresponding phosphorylated products in high yields. As a key step, this new method was applied to the synthesis of anticancer drug Combretastatin-A4, significantly shortening its synthetic path.
The synthesis of (E) and (Z)-combretastatins A-4 and a phenanthrene from Combretum caffrum
Lawrence, Nicholas J.,Ghani, Fazni Abdul,Hepworth, Lucy A.,Hadfield, John A.,McGown, Alan T.,Pritchard, Robin G.
, p. 1656 - 1660 (2007/10/03)
The synthesis of the trans stilbene E-combretastatin A-4 has been achieved via a Horner-Wittig reaction of (3,4,5- trimethoxybenzyl)diphenylphosphine oxide. The anticancer drug Z- combretastatin A-4 was prepared by the hydroboration/protonation of a diaryl- alkyne.
Efficient synthesis of benzylphosphine oxides and E-stilbenes
Brown,Brown, Karen M.,Lawrence,Lawrence, Nicholas J.,Liddle,Liddle, John,Muhammad,Muhammad, Faiz,Jackson,Jackson, David A.
, p. 6733 - 6736 (2007/10/02)
A series of substituted benzylphosphine oxides has been synthesized by reduction of the corresponding (α-chlorobenzyl)phosphine oxide, derived from the benzaldehyde and chlorodiphenylphosphine, with either sodium borohydride (DMSO, 60-70 °C, 12 h) or tributyltin hydride and AIBN (C6H6, 80 °C, 2 h). Reaction of the (α-lithiobenzyl)phosphine oxide with aldehydes gave exclusively E-alkenes.
