Transition-Metal-Free Addition of Dialkyl Phosphites to Phthalazin-2-ium Bromide: Synthesis of α-Aminophosphonate Analogues.

Qian Chen, Xuanming Zheng, Fang Guo, Kun Liang, Fanrui Zhou

The Journal of organic chemistry 2021 Dec 17

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α-Aminophosphonate analogues containing a phthalazine skeleton were efficiently obtained by a new transition-metal-free addition of dialkyl phosphites to phthalazin-2-ium bromide under mild conditions. A mechanistic study using isotope labeling and radical inhibition experiment revealed that the present transformation passes through a nucleophilic addition of dialkyl phosphates, rather than an insertion of P-H to carbenes.

Citation

Qian Chen, Xuanming Zheng, Fang Guo, Kun Liang, Fanrui Zhou. Transition-Metal-Free Addition of Dialkyl Phosphites to Phthalazin-2-ium Bromide: Synthesis of α-Aminophosphonate Analogues. The Journal of organic chemistry. 2021 Dec 17;86(24):18278-18286