Synthesis of Diarylalkanes by Photoreductive 1,2-Diarylation of Alkenes with Aryl Halides and Cyanoaromatics
We report a visible light-induced photoreductive strategy for three-component diarylation of alkenes with aryl halides and cyanoaromatics. Upon photoredox catalysis and with tertiary alkyl amines as the electron transfer agent, aryl halides selectively undergo halogen atom transfer to 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 addition and radical-radical coupling fashion to rapidly assemble diverse functionalized polyarylalkanes with high regio- and chemoselectivity. This method can be applied to broad feedstocks, including terminal alkenes, internal alkenes, aryl iodides, aryl bromides, aryl chlorides, electron-deficient benzonitriles, and isonicotinonitriles.
Authors
- Xuan‐Hui Ouyang (ORCID: https://orcid.org/0000-0002-5018-881X)
- Jin‐Heng Li (ORCID: https://orcid.org/0000-0001-7215-7152)
- Liang Zeng (ORCID: https://orcid.org/0009-0000-3012-4651)
- Deliang He (ORCID: https://orcid.org/0000-0003-1298-8864)
Institutions
- Qingdao University of Science and Technology (CN)
- Hunan University (CN)
- State Key Laboratory of Chemobiosensing and Chemometrics (CN)
- Henan Normal University (CN)
- Lanzhou University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-09-05
- DOI
- https://doi.org/10.1021/acs.joc.4c01830
- Citations
- 11
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 2.75
Funders
- Henan Normal University
- National Natural Science Foundation of China