Nickel-Catalyzed Reductive Dicarbofunctionalization\nof 1,3-Dienes with Aziridines and (Het)Aryl Electrophiles

A three-component\nreductive 1,4-dicarbofunctionalization of 1,3-dienes\nwith aziridines and (het)aryl electrophiles was realized. The combination\nof Ni catalysis with Mn powder as a final reductant enables the direct\nformation of a Csp<sup>2</sup>–Csp<sup>3</sup> and a Csp<sup>3</sup>–Csp<sup>3</sup> bond at one time. This protocol afforded\na convenient approach to the synthesis of β-arylethylamines\nbearing various functionals and heterocyclic groups. The utility of\nthis reaction was also demonstrated by scale-up preparation, late-stage\nmodification of bioactive molecules, and diverse transformations.

Publication Details

Journal
Figshare
Published
2024-09-26
DOI
https://doi.org/10.1021/acs.orglett.4c02983.s001
Primary Topic
Catalytic C–H Functionalization Methods
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article
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article

Nickel-Catalyzed Reductive Dicarbofunctionalization\nof 1,3-Dienes with Aziridines and (Het)Aryl Electrophiles

Figshare
Catalytic C–H Functionalization Methods
article

Nickel-Catalyzed Reductive Dicarbofunctionalization\nof 1,3-Dienes with Aziridines and (Het)Aryl Electrophiles

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Abstract

A three-component\nreductive 1,4-dicarbofunctionalization of 1,3-dienes\nwith aziridines and (het)aryl electrophiles was realized. The combination\nof Ni catalysis with Mn powder as a final reductant enables the direct\nformation of a Csp<sup>2</sup>–Csp<sup>3</sup> and a Csp<sup>3</sup>–Csp<sup>3</sup> bond at one time. This protocol afforded\na convenient approach to the synthesis of β-arylethylamines\nbearing various functionals and heterocyclic groups. The utility of\nthis reaction was also demonstrated by scale-up preparation, late-stage\nmodification of bioactive molecules, and diverse transformations.

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Catalytic C–H Functionalization Methods
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Nickel-Catalyzed Reductive Dicarbofunctionalization\nof 1,3-Dienes with Aziridines and (Het)Aryl Electrophiles · Figshare (2024) | TGRS Research Map | TGRS