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A Neutral PC_NHCP Co(I)-Me Pincer Complex as a Catalyst for N-Allylic Isomerization with a Broad Substrate Scope.

ABSTRACT: Earth-abundant-metal catalyzed double bond transposition offers a sustainable and atom-economical route toward the synthesis of internal alkenes. With an emphasis specifically on internal olefins and ethers, the isomerization of allylic amines has been particularly under represented in the literature. Herein, we report an efficient methodology for the selective isomerization of N-allylic organic compounds, including amines, amides, and imines. The reaction is catalyzed by a neutral PC_NHCP cobalt(I) pincer complex and proceeds via a π-allyl mechanism. The isomerization occurs readily at 80-90 °C, and it is compatible with a wide variety of functional groups. The in situ formed enamines could additionally be used for a one-pot inverse-electron-demand Diels-Alder reaction to furnish a series of diversely substituted heterobiaryls, which is further discussed in this report.

SUBMITTER: Raje S

PROVIDER: S-EPMC11002938 | biostudies-literature | 2024 Apr

REPOSITORIES: biostudies-literature

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A Neutral PCNHCP Co(I)-Me Pincer Complex as a Catalyst for N-Allylic Isomerization with a Broad Substrate Scope.

Raje Sakthi S Sheikh Mohammad Tofayel T de Ruiter Graham G

The Journal of organic chemistry 20240323 7

Earth-abundant-metal catalyzed double bond transposition offers a sustainable and atom-economical route toward the synthesis of internal alkenes. With an emphasis specifically on internal olefins and ethers, the isomerization of allylic amines has been particularly under represented in the literature. Herein, we report an efficient methodology for the selective isomerization of N-allylic organic compounds, including amines, amides, and imines. The reaction is catalyzed by a neutral PC<sub ...[more]

PMID: 38520345

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