Palladium-catalyzed Heck cyclization/carbonylation with formates: synthesis of azaindoline-3-acetates and furoazaindolines

Abstract

We reported herein a palladium-catalyzed domino cyclization/carbonylation to access ester functionalized azaindolines, applying formates as convenient carbonyl source. All four azaindoline isomers were constructed, and exhibiting good functional group compatibility....

Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes

“…Wu and co-workers have elaborated a method for the synthesis of a range of isomeric azaindolines 23 by reacting aminopyridines and phenyl formates promoted by Pd(TFA) 2 and L4. [107] Selected results are collected in Scheme 81. Ring formation took place via domino Heck reaction followed by carbonylation with formates generating ester functions at C-3 leading to deliver 7-azaindoline derivatives with low to high yields (Scheme 81).…”

“…Wu and co‐workers have elaborated a method for the synthesis of a range of isomeric azaindolines 23 by reacting aminopyridines and phenyl formates promoted by Pd(TFA) 2 and L 4 [107] . Selected results are collected in Scheme 81.…”

Palladium-Catalyzed Heck Cyclization with P(O)H Compounds to Construct Phosphinonyl-Azaindoline and -Azaoxindole Derivatives

“…High-resolution mass spectral analysis (HRMS) data were measured on a Bruker Apex II instrument. Substrates 1 were synthesized according to literature . Phosphorus reagents 2 were purchased from commercial suppliers.…”

Highly regioselective C–H carbonylation of alkenes with phenyl formateviaaryl to vinyl 1,4-palladium migration

“…In order to avoid the usage of toxic CO gas in carbonylative reactions, phenyl formate is the desirable CO source due to its commercial availability, low cost and low toxicity. 15 Herein, we report the successful carbonylation of the vinyl C–H bond using phenyl formate as the CO source via an aryl to vinyl 1,4-palladium migration, providing an efficient and convenient approach to access highly stereoselective β,β-diaryl substituted α,β-unsaturated esters (Scheme 1c).…”