Synthesis of Diarylalkanes\nby Photoreductive 1,2-Diarylation\nof Alkenes with Aryl Halides and Cyanoaromatics

We report a visible light-induced\nphotoreductive strategy for three-component\ndiarylation of alkenes with aryl halides and cyanoaromatics. Upon\nphotoredox catalysis and with tertiary alkyl amines as the electron\ntransfer agent, aryl halides selectively undergo halogen atom transfer\nto generate the aryl radicals and two C(sp<sup>2</sup>)–C(sp<sup>3</sup>) bonds between the cabron atoms are created in a radical\naddition and radical–radical coupling fashion to rapidly assemble\ndiverse functionalized polyarylalkanes with high regio- and chemoselectivity.\nThis method can be applied to broad feedstocks, including terminal\nalkenes, internal alkenes, aryl iodides, aryl bromides, aryl chlorides,\nelectron-deficient benzonitriles, and isonicotinonitriles.

Publication Details

Journal
Figshare
Published
2024-09-05
DOI
https://doi.org/10.1021/acs.joc.4c01830.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Synthesis of Diarylalkanes\nby Photoreductive 1,2-Diarylation\nof Alkenes with Aryl Halides and Cyanoaromatics

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Radical Photochemical Reactions
article

Synthesis of Diarylalkanes\nby Photoreductive 1,2-Diarylation\nof Alkenes with Aryl Halides and Cyanoaromatics

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Abstract

We report a visible light-induced\nphotoreductive strategy for three-component\ndiarylation of alkenes with aryl halides and cyanoaromatics. Upon\nphotoredox catalysis and with tertiary alkyl amines as the electron\ntransfer agent, aryl halides selectively undergo halogen atom transfer\nto generate the aryl radicals and two C(sp<sup>2</sup>)–C(sp<sup>3</sup>) bonds between the cabron atoms are created in a radical\naddition and radical–radical coupling fashion to rapidly assemble\ndiverse functionalized polyarylalkanes with high regio- and chemoselectivity.\nThis method can be applied to broad feedstocks, including terminal\nalkenes, internal alkenes, aryl iodides, aryl bromides, aryl chlorides,\nelectron-deficient benzonitriles, and isonicotinonitriles.

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Radical Photochemical Reactions
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