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Pyridine Wingtip in [Pd(Py-tzNHC)2]2+ Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes.

ABSTRACT: The cationic palladium(II) complex 1 of pyridyl-mesoionic carbene ligand catalyzes Markovnikov-selective intermolecular hydroamination between anilines and terminal alkynes into the corresponding imines. The reaction proceeds at room temperature, in the absence of additives, with exquisite selectivity and diverse functional group tolerance. The key intrinsic feature of the catalyst is the pyridine wingtip confined to the proximity of the alkynophilic metal active site, which mimics the function of enzyme-like architectures by assisting entropically favored proton transfers.

SUBMITTER: Virant M 

PROVIDER: S-EPMC7308070 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Pyridine Wingtip in [Pd(Py-<i>tz</i>NHC)<sub>2</sub>]<sup>2+</sup> Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes.

Virant Miha M   Mihelač Mateja M   Gazvoda Martin M   Cotman Andrej E AE   Frantar Anja A   Pinter Balazs B   Košmrlj Janez J  

Organic letters 20200130 6

The cationic palladium(II) complex <b>1</b> of pyridyl-mesoionic carbene ligand catalyzes Markovnikov-selective intermolecular hydroamination between anilines and terminal alkynes into the corresponding imines. The reaction proceeds at room temperature, in the absence of additives, with exquisite selectivity and diverse functional group tolerance. The key intrinsic feature of the catalyst is the pyridine wingtip confined to the proximity of the alkynophilic metal active site, which mimics the fu  ...[more]