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Redox-Neutral Nickel-Catalyzed Cross-Coupling Reactions of (Homo)allylic Alcohols and Aryltriflates

Xuchao Wang, Feipeng Liu, Zijuan Yan, Qing Qiang, Wei Huang, Zi‐Qiang Rong

2021ACS Catalysis24 citationsDOI

Abstract

Herein, we report a redox-neutral Ni-catalyzed cross-coupling reaction of two readily available precursors to produce the corresponding ketones that are an important structural motif in numerous biologically active entities. By the use of a commercially available nickel/Triphos catalytic system, a range of easily accessible alkenyl primary alcohols and aryltriflates can be converted in a rapidly assembled fashion to valuable ketones with good yields and wide functional group tolerance. We also demonstrate the utility of this transformation by late-stage functionalization of a large set of complex molecules with good efficiency, which offers a distinct entry to more functionalized aromatic ketones.

Topics & Concepts

Allylic rearrangementCatalysisNickelChemistryRedoxCombinatorial chemistryCoupling reactionMoleculeFunctional groupPrimary (astronomy)Structural motifOrganic chemistryAstronomyPhysicsPolymerBiochemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis