23073-11-2Relevant academic research and scientific papers
Aminopalladation-triggered carbene insertion reaction: Synthesis of 2-(1H-indol-3-yl)acetates
Hu, Ziwei,Luo, Shuang,Zhu, Qiang
, p. 1060 - 1064 (2015)
The first example of a nucleopalladation-triggered carbene insertion reaction for the synthesis of C-3 alkylated indole derivatives from ortho-alkynyltrifluoroacetanilides and α-diazoacetates is presented; it involves a palladium catalyst and a weak base in the open air. Yields range from 49-88% with excellent functional group tolerance. The reaction proceeds through intramolecular aminopalladation of alkynes followed by carbene insertion. Migratory insertion of the carbene into the σ-indolylpalladium intermediate was favored over N-H insertion.
