Nickel-catalyzed reductive cross-coupling of aryl halides with alkyl halides.
The direct reductive cross-coupling of alkyl halides with aryl halides is described. The transformation is efficient (equimolar amounts of the starting materials are used), generally high-yielding (all but one between 55 and 88% yield), highly functional-group-tolerant [OH, NHBoc, NHCbz, Bpin, C(O)Me, CO(2)Et, and CN are all tolerated], and easy to perform (uses only benchtop-stable reagents, tolerates small amounts of water and oxygen, changes color when complete, and uses filtration workup). The reaction appears to avoid the formation of intermediate organomanganese species, and a synergistic effect was found when a mixture of two ligands was employed.
Everson
Daniel A
DA
Department of Chemistry, University of Rochester, Rochester, New York 14627, USA.
Shrestha
Ruja
R
Weix
Daniel J
DJ
D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism
D006841:Hydrocarbons, Aromatic; D006846:Hydrocarbons, Halogenated; D009532:Nickel