3 years ago

Pd-Catalyzed Carbonylative Carboperfluoroalkylation of Alkynes. Through-Space 13C–19F Coupling as a Probe for Configuration Assignment of Fluoroalkyl-Substituted Olefins

Pd-Catalyzed Carbonylative Carboperfluoroalkylation of Alkynes. Through-Space 13C–19F Coupling as a Probe for Configuration Assignment of Fluoroalkyl-Substituted Olefins
Sylwester Domański, Wojciech Chaładaj, Olga Staszewska-Krajewska
A four-component Pd-catalyzed protocol for direct synthesis of perfluoroalkyl-substituted enones is reported. Under mild conditions and low catalyst loading, alkynes, iodoperfluoroalkanes, (hetero)arylboronic acids, and carbon monoxide are assembled into highly elaborate products with good yields and excellent regio- and stereoselectivities. The configuration of the products was confirmed by the observation of through-space 13C–19F couplings, accessible through the analysis of routine 13C NMR spectra.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01236

DOI: 10.1021/acs.joc.7b01236

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