The Journal of Organic Chemistry · 2014 · 118 citations · 40 references
Natural SciencesChemistryInorganic ChemistryOrganic ChemistryOrganometallic ChemistryCoordination ChemistryCross-coupling ReactionsHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsAryl Halide CouplingCross CouplingFunctional Group ToleranceHeterocycle FunctionalizationHeterocyclic ReactivityLate-stage Functionalization Via Cross-couplingNickel-catalyzed Cross-couplingReductive Cross-coupling
Reductive cross-coupling allows the direct C-C bond formation between two organic halides without the need for preformation of an organometallic reagent. A method has been developed for the reductive cross-coupling of nonaromatic, heterocyclic bromides with aryl or heteroaryl bromides. The developed conditions use an air-stable Ni(II) source in the presence of a diamine ligand and a metal reductant to allow late-stage incorporation of saturated heterocyclic rings onto aryl halides in a functional-group tolerant manner.
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Daniel A. Everson, Brittany A. Jones, Daniel J. Weix · Journal of the American Chemical Society · 2012 · 419 citations · Full text