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Aminopalladation‐Triggered Carbene Insertion Reaction: Synthesis of 2‐(1 H ‐Indol‐3‐yl)acetates
Author(s) -
Hu Ziwei,
Luo Shuang,
Zhu Qiang
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400799
Subject(s) - carbene , chemistry , insertion reaction , intramolecular force , migratory insertion , indole test , catalysis , alkylation , functional group , medicinal chemistry , palladium , photochemistry , combinatorial chemistry , stereochemistry , organic chemistry , polymer
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 NH insertion.