Electrochemical Dehydrogenative [3 + 2]/[5 + 2] Annulation of <i>N</i>-Arylacrylamides with γ,σ-Unsaturated Malonates via Direct C(sp<sup>3</sup>)–H/C(sp<sup>2</sup>)–H Functionalization
Herein, we introduce an electrochemical dehydrogenative [3 + 2]/[5 + 2] annulation of easily available <i>N</i>-arylacrylamides with γ,σ-unsaturated malonates through C(sp<sup>3</sup>)-H/C(sp<sup>2</sup>)-H functionalization. The employment of inexpensive ferrocene as the redox catalyst allows access to diverse benzo[<i>b</i>]azepin-2-ones in moderate to excellent yields without stoichiometric oxidants. This protocol features broad substrate scope and excellent selectivity, and mechanistic studies indicated that the reaction proceeded through the oxidation of a C(sp<sup>3</sup>)-H bond to generate an alkyl radical, radical addition across the C═C bond, [3 + 2]/[5 + 2] annulations, and C(sp<sup>2</sup>)-H functionalization cascades.
Authors
- Yuting Cai (ORCID: https://orcid.org/0000-0002-1758-0086)
- Qi Xue (ORCID: https://orcid.org/0000-0003-0562-9265)
- Jin‐Heng Li (ORCID: https://orcid.org/0000-0001-7215-7152)
- Wenyu Zhang (ORCID: https://orcid.org/0000-0002-1924-6591)
- Yang Li (ORCID: https://orcid.org/0000-0001-6026-4794)
- Qiu-Hua Xu
- Xia-Lu Cheng
Institutions
- Qingdao University of Science and Technology (CN)
- Nanchang Hangkong University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-08-19
- DOI
- https://doi.org/10.1021/acs.orglett.4c02163
- Citations
- 5
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- National Natural Science Foundation of China
- Jiangxi Provincial Department of Science and Technology