Premium
Palladium‐Catalyzed Decarboxylative Generation and Propargylation of 2‐Azaallyl Anions
Author(s) -
Tang Shaojian,
Wei Wenjing,
Yin Dan,
Poznik Michal,
Chruma Jason J.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900537
Subject(s) - chemistry , propargyl , catalysis , palladium , allene , imine , aryl , diene , solvent , organic chemistry , combinatorial chemistry , polymer chemistry , alkyl , natural rubber
A palladium‐catalyzed decarboxylative propargylation (DcPg) of propargyl 2,2‐diphenylglycinate imines was developed. In this process, the nature of the propargyl ester and aryl imine components, as well as the catalyst system and solvent, had a significant impact on the ratio of desired propargylated products vs. allene and/or diene side products that arise via different modes of C–C bond formation. The resulting propargylated products can be transformed readily into useful ( Z )‐homoallylic amines. Moreover, the regioisomeric diene products could be converted to pharmaceutically‐relevant diarylmethyl imines via a two‐step Diels‐Alder/oxidation process.