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Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex.

ABSTRACT: A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using ?-aminoketonato- and ?-diketiminato-based pincer-type nickel(II) complexes as catalysts. An ?-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, allylbenzene derivatives, in high yield. The regioselective reaction of a variety of substituted cinnamyl ethers proceeded to give the corresponding linear products. In contrast, ?- and ?-alkyl substituted allylic ethers afforded a mixture of the linear and branched products. These results indicated that the coupling reaction proceeded via a ?-allyl nickel intermediate.

SUBMITTER: Hashimoto T 

PROVIDER: S-EPMC6631569 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex.

Hashimoto Toru T   Funatsu Kei K   Ohtani Atsufumi A   Asano Erika E   Yamaguchi Yoshitaka Y  

Molecules (Basel, Switzerland) 20190621 12

A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, allylbenzene derivatives, in high yield. The regioselective reaction of a variety of substituted cinnamyl ethers proceeded to give the corresp  ...[more]

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