Electrochemical 1,2-Alkylarylation of Styrenes with Malonates and <i>N</i>-Heteroarenes via Direct C(sp<sup>3</sup>)–H/C(sp<sup>2</sup>)–H Functionalization
A general and atom-economical electrochemical dehydrogenative method for the intermolecular 1,2-alkylarylation of styrenes with malonates and nucleophilic <i>N</i>-heteroarenes (including indoles and pyrroles) has been developed. This transformation provides a regioselective route to construct highly valuable 1,1-diarylalkanes enabled by C(sp<sup>3</sup>)-H/C(sp<sup>2</sup>)-H functionalization under mild conditions, and H<sub>2</sub> is the only theoretical byproduct. Mechanistic studies indicated that the reaction proceeded through the oxidative of the C(sp<sup>3</sup>)-H bond to generate alkyl radical, radical addition across the C═C bond, single electron oxidation and C(sp<sup>2</sup>)-H functionalization cascades.
Authors
- Jin‐Heng Li (ORCID: https://orcid.org/0000-0001-7215-7152)
- Yilin Liu (ORCID: https://orcid.org/0000-0002-8491-914X)
- Qi Xue (ORCID: https://orcid.org/0000-0002-8987-9634)
- Tingting Zhang (ORCID: https://orcid.org/0000-0001-7560-1394)
- Wenyu Zhang (ORCID: https://orcid.org/0000-0002-1924-6591)
- Yang Li (ORCID: https://orcid.org/0000-0001-6026-4794)
- Xiao Ni Zhong
Institutions
- Huaihua University (CN)
- Qingdao University of Science and Technology (CN)
- Institute of Organic Synthesis (RU)
- Laboratoire de Synthèse Organique (FR)
- State Key Laboratory of Chemical Engineering (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-02-26
- DOI
- https://doi.org/10.1021/acs.joc.4c02803
- Citations
- 5
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 4.68
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Hunan Province
- Taishan Scholar Project of Shandong Province
- Jiangxi Provincial Department of Science and Technology