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Nitrogen-Atom Insertion of Indolyl Phosphonium Salts through C-P and C-C Bond Functionalization
Qian Tong1, Qin Ma1, Yao-Qi Yang1
1Technical Institute of Fluorochemistry, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
None:
Precise nitrogen-atom insertion into an inert C-C bond is a powerful skeletal editing strategy for accessing valuable nitrogen-containing compounds. However, a majority of the works focus on the transformation of cyclic systems. Herein, a base-promoted nitrogen-atom insertion into indolyl phosphonium salts through C-P bond functionalization and selective C-C bond cleavage was developed for the synthesis of structurally important 3-aminoindoles. The reaction features a broad substrate scope, excellent functional group tolerance, and good scalability under mild reaction conditions. In addition, the procedural simplicity and synthetic accessibility of the protocol were demonstrated by a one-pot, two-step procedure commencing from indole and aldehyde without the need for the presynthesis of the indolyl phosphonium salt.
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