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Palladium Catalysts for Highly Selective Sonogashira Reactions of Aryl and Heteroaryl Bromides
Author(s) -
Torborg Christian,
Zapf Alexander,
Beller Matthias
Publication year - 2008
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.200700004
Subject(s) - sonogashira coupling , aryl , palladium , catalysis , chemistry , tetramethylethylenediamine , combinatorial chemistry , turnover number , organic chemistry , medicinal chemistry , alkyl
Palladium catalysts have been studied for the Sonogashira–Hagihara coupling of aryl and heteroaryl bromides with terminal alkynes. Among the different biarylphosphines tested, 2‐(di‐ tert ‐butylphosphino)‐ N ‐phenylindole (cata C Xium PIntb) allows the efficient coupling of both activated and deactivated (hetero)aryl bromides in the presence of sodium tetrachloropalladate in tetramethylethylenediamine (TMEDA) at 80 °C. The catalyst system gives high turnover numbers (up to 14 100) and shows a broad tolerance towards functional groups such as OH and NH 2 , as well as heterocycles.