Photoinduced EDA Complexes Enabled C(sp<sup>2</sup>)–OMe Bond Cleavage and Cyanation of Electron-Rich Arenes
Herein, an EDA complex enabling C(sp<sup>2</sup>)-OMe bond cleavage and cyanation was established by using 1,4-dicyanobenzene as both an electron-deficient acceptor and a low-toxicity cyanide source. Mechanistic studies revealed the role of double EDA complexes in forming the cyanide anion and aromatic cation radical intermediate, leading to a diverse array of valuable aryl nitrile derivatives in good to excellent yields. Furthermore, late-stage functionalization of biorelevant compounds and gram-scale synthesis demonstrate the utility of this methodology.
Authors
- Siping Wei (ORCID: https://orcid.org/0000-0002-1084-8772)
- Aiyun Luo (ORCID: https://orcid.org/0000-0001-9880-8259)
- Bowen Lei (ORCID: https://orcid.org/0000-0003-4980-6702)
- Jun Zhou (ORCID: https://orcid.org/0000-0003-4353-1621)
- Junliang Yang (ORCID: https://orcid.org/0000-0002-5553-0186)
- Wenjie Liu (ORCID: https://orcid.org/0000-0002-4907-2465)
- Sijia Zhang
- Xia Zhou (ORCID: https://orcid.org/0000-0001-9170-1504)
- Xi Du
Institutions
- Southwest Medical University (CN)
- Pharmaceutical Biotechnology (Czechia) (CZ)
- Zhejiang University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-16
- DOI
- https://doi.org/10.1021/acs.orglett.5c01967
- Citations
- 1
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94