Premium
The Sonogashira Coupling of Polymer‐Supported Propargylamine with Aryl Iodides
Author(s) -
Leikoski Tuomo,
Kallonen Sirkku,
YliKauhaluoma Jari
Publication year - 2010
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200900129
Subject(s) - chemistry , sonogashira coupling , aryl , linker , amine gas treating , polymer , carbamate , combinatorial chemistry , palladium , catalysis , polymer chemistry , organic chemistry , computer science , operating system , alkyl
The Sonogashira coupling reaction of polymer‐supported propargylamine (=prop‐2‐yn‐1‐amine) with aryl iodides in the presence of the [Pd(PPh 3 ) 2 ]Cl 2 /CuI catalyst system produces 3‐arylprop‐1‐yn‐1‐amines smoothly at room temperature ( Scheme ). When propargylamine is attached on Wang resin through a carbamate linker, the common problems with amino functionality in palladium‐catalyzed couplings are overcome. The arylpropynamines are cleaved from the polymer with CF 3 COOH and converted into chromatographically easily separable acetamides. Our solid‐phase method opens a new pathway toward precursors of pharmacologically interesting arylpropynamines and arylpropanamines.