Base-Catalyzed Hydrophosphination of Azobenzenes with Diarylphosphine Oxides: A Precise Construction of N-N-P Unit

作者：Hong, Gang; Zhu, Xiaoyan; Hu, Chen; Arum, Alfred Njasotapher; Wu, Shengying^*; Wang, Limin^*

来源：Journal of Organic Chemistry, 2016, 81(15): 6867-6874.

DOI：10.1021/acs.joc.6b01210

• AROMATIC AZO-COMPOUNDS
• N=N BOND
• C-P
• PHOSPHINIC AMIDES
• H-PHOSPHONATES
• CLEAVAGE
• FUNCTIONALIZATION
• ACCESS
• HYDROGENATION
• CYCLIZATION

Addition of diarylphosphine oxides to the N=N double bond of azobenzenes leads to the formation of the P-substituted hydrazines in up to 98% yield for 24 examples, and the formation of diphenylphosphinic amides was observed in three substrates. This strategy features tolerance of a wide range of functional groups, simple operation, and mild reaction conditions. Specially, this method can be also applied to the gram-scale synthesis of the product. A polar reaction mechanism is also proposed based on control experiments.

• 出版日期2016-8-5
• 单位华东理工大学