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N-Heterocyclic Carbene Ligand-Controlled Regioselectivity for Nickel-Catalyzed Hydroarylation of Vinylarenes with Benzothiazoles.

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A facile regioselective switch for nickel-catalyzed hydroarylation of vinylarenes with benzothiazoles has been developed, which relies on the simple structural variation of novel Ni(II) complexes of the type Ni(NHC)[P(OR)3]Br2. Using… Click to show full abstract

A facile regioselective switch for nickel-catalyzed hydroarylation of vinylarenes with benzothiazoles has been developed, which relies on the simple structural variation of novel Ni(II) complexes of the type Ni(NHC)[P(OR)3]Br2. Using magnesium turnings as the reductant, Ni(IMes)[P(OEt)3]Br2 afforded branched products, while Ni(IPr*OMe)[P(OEt)3]Br2 created steric demand to afford linear products. This work also provides a rare example of the rational design of heteroleptic Ni(II) complexes that display the required air stability, reactivity, and regioselectivity via synergism between NHC and phosphite ligands.

Keywords: catalyzed hydroarylation; nickel catalyzed; hydroarylation vinylarenes; vinylarenes benzothiazoles

Journal Title: Organic letters
Year Published: 2019

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