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A General Protocol for Robust Sonogashira Reactions in Micellar Medium
Author(s) -
Jakobi Markus,
Gallou Fabrice,
Sparr Christof,
Parmentier Michael
Publication year - 2019
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.201900024
Subject(s) - chemistry , sonogashira coupling , alkyne , catalysis , aryl , combinatorial chemistry , aqueous solution , halide , selectivity , coupling reaction , aqueous medium , organic chemistry , palladium , alkyl
Abstract A robust and general protocol for a sustainable copper‐free Sonogashira cross coupling under micellar aqueous reaction conditions with high turnover was developed. By using the commercially available catalyst CataCXium A Pd G3 and THF as co‐solvent, various alkyne substrates were efficiently cross‐coupled with a broad range of aryl halides, providing improved yields and low catalyst loadings. The reaction parameters were optimized to render the process operationally simple, robust and scalable. The method gives access to alkynylated arenes, heterocyclic compounds, and monofunctionalized products from dihalogenated substrates with an improved selectivity achieved by the micellar aqueous reaction conditions.