3 years ago

Palladium(I) Dimer Enabled Extremely Rapid and Chemoselective Alkylation of Aryl Bromides over Triflates and Chlorides in Air

Palladium(I) Dimer Enabled Extremely Rapid and Chemoselective Alkylation of Aryl Bromides over Triflates and Chlorides in Air
Theresa Sperger, Franziska Schoenebeck, Thomas Scattolin, Indrek Kalvet, Guillaume Magnin
Disclosed herein is the first general chemo- and site-selective alkylation of C−Br bonds in the presence of COTf, C−Cl and other potentially reactive functional groups, using the air-, moisture-, and thermally stable dinuclear PdI catalyst, [Pd(μ-I)PtBu3]2. The bromo-selectivity is independent of the substrate and the relative positioning of the competing reaction sites, and as such fully predictable. Primary and secondary alkyl chains were introduced with extremely high speed (<5 min reaction time) at room temperature and under open-flask reaction conditions. Pick me! A method for cross-coupling bromo groups with Grignard or organozinc reagents mediated by a dinuclear PdI catalyst was developed. The reactions were highly selective for C−Br and were tolerant of both C−OTf and C−Cl functionalities. The transformations proceeded under open-flask conditions at room temperature, and were complete within 5 min.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201701691

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