Copper-catalyzed oxidative phosphonoheteroarylation of alkenes with phosphonates and N-heteroarenes via P-H/C-H functionalization

作者：Xu, Chong-Hui; Xiong, Zhi-Qiang; Li, Yang; Zhu, Yan-Ping^*; Li, Jin-Heng^*

来源：Organic Chemistry Frontiers, 2022, 9(2): 476-480.

DOI：10.1039/d1qo01644j

• ORGANOPHOSPHORUS COMPOUNDS
• PHOSPHINE OXIDES
• CASCADE CYCLIZATION
• UNACTIVATED ALKENES
• FACILE SYNTHESIS
• P(O)-H COMPOUNDS
• DIFUNCTIONALIZATION
• HYDROPHOSPHINATION
• PHOSPHORYLATION

A copper-catalyzed oxidative intermolecular phosphonoheteroarylation of alkenes with phosphonates and nucleophilic N-heteroarenes (such as indoles and pyrroles) involving P-H/C-H functionalization for the synthesis of highly valuable beta-(N-heteroaryl)-alkylphosphonates is disclosed. This method allows the incorporation of two functional groups, a phosphonate and a N-heteroarene, into the alkene in a single reaction step through oxidative formation of the P-centered radicals, addition across the C=C bond, single electron oxidation and C-H functionalization cascades.

• 单位
  南昌航空大学; 烟台大学; 兰州大学