Visible-Light-Mediated\nThree-Component Decarboxylative\nCoupling Reactions for the Synthesis of 4‑Alkylpyridines

4-Alkylation of pyridines has been achieved by a photocatalyzed\nthree-component reaction of an olefin, an aryloxyacetic acid, and\ncyanopyridine using Ir[dF(CF<sub>3</sub>)ppy]<sub>2</sub>(dtbbpy)PF<sub>6</sub> as a photocatalyst. In this way, a new type of 4-alkylpyridines\nbearing aryl and aryloxy substituents on the phenyl was accessed with\npotential pharmaceutical value. In addition to mild reaction conditions,\nthe method has several other advantages, including a multicomponent\none-pot protocol, good functional group tolerance, and easy amplification\nof the reaction scale. The reaction mechanism has been clarified by\ncontrol experiments and computation of the reaction energy profile.

Publication Details

Journal
Figshare
Published
2024-11-14
DOI
https://doi.org/10.1021/acs.joc.4c02037.s001
Primary Topic
Computational Physics and Python Applications
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article
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article

Visible-Light-Mediated\nThree-Component Decarboxylative\nCoupling Reactions for the Synthesis of 4‑Alkylpyridines

Figshare
Computational Physics and Python Applications
article

Visible-Light-Mediated\nThree-Component Decarboxylative\nCoupling Reactions for the Synthesis of 4‑Alkylpyridines

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Abstract

4-Alkylation of pyridines has been achieved by a photocatalyzed\nthree-component reaction of an olefin, an aryloxyacetic acid, and\ncyanopyridine using Ir[dF(CF<sub>3</sub>)ppy]<sub>2</sub>(dtbbpy)PF<sub>6</sub> as a photocatalyst. In this way, a new type of 4-alkylpyridines\nbearing aryl and aryloxy substituents on the phenyl was accessed with\npotential pharmaceutical value. In addition to mild reaction conditions,\nthe method has several other advantages, including a multicomponent\none-pot protocol, good functional group tolerance, and easy amplification\nof the reaction scale. The reaction mechanism has been clarified by\ncontrol experiments and computation of the reaction energy profile.

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