Tunable Trifunctionalization of Tertiary Enaminones for the Regioselective and Metal-Free Synthesis of Discrete and Proximal Phosphoryl Nitriles.

This paper reports an unprecedented trifunctionalization of tertiary enaminones for the synthesis phosphoryl nitriles by the reactions of enaminones with diarylphosphine oxides and trimethylsilyl cyanide (TMSCN) without the use of any metal reagent. Employing tetrabutyl ammonium hydroxide (TBAH) as the catalyst (0.2 equiv) enables discrete cyanophosphonation. On the other hand, selective proximal cyanophosphonation has been realized in the presence of acetic acid only (AcOH).

Citation

Zhongrong Xu, Leiqing Fu, Xia Fang, Bin Huang, Liyun Zhou, Jie-Ping Wan. Tunable Trifunctionalization of Tertiary Enaminones for the Regioselective and Metal-Free Synthesis of Discrete and Proximal Phosphoryl Nitriles. Organic letters. 2021 Jul 02;23(13):5049-5053

PMID: 34137270

search → result