Palladium Catalysts for Highly Selective Sonogashira Reactions of Aryl and Heteroaryl Bromides | Zendy

Torborg Christian | Zendy; Zapf Alexander | Zendy; Beller Matthias | Zendy

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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.

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