Base-Mediated Formal Denitrogenative Insertion of Nonactivated Triazoles into Aldehydes: Stereospecific Synthesis of Highly Substituted Acrylamides
A base-mediated denitrogenative insertion of nonactivated <i>N(1)</i>-aryl-1,2,3-triazoles into aldehydes to construct trisubstituted (<i>E</i>)-acrylamides was developed. The reaction, which involves formal insertion of two atoms from the triazole into the aldehyde C═O bond with concomitant loss of nitrogen, proceeds at ambient temperature with complete stereocontrol. This method provides a highly efficient and straightforward means to construct functionalized acrylamides by employing readily available 1,2,3-triazoles and aldehydes as starting materials.
Authors
- Xian Dong (ORCID: https://orcid.org/0000-0001-7639-1800)
- S. WANG
- Zhu Wenxiang
- Guiping Qin (ORCID: https://orcid.org/0000-0002-5510-2376)
- Yubo Jiang (ORCID: https://orcid.org/0009-0003-1159-8802)
- Tiebo Xiao (ORCID: https://orcid.org/0000-0003-0799-1049)
- Edward A. Anderson (ORCID: https://orcid.org/0000-0002-4149-0494)
- L. Teng
Institutions
- Kunming University of Science and Technology (CN)
- Yunnan University (CN)
- University of Oxford (GB)
- Pharmaceutical Biotechnology (Czechia) (CZ)
- Yunnan University of Traditional Chinese Medicine (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-13
- DOI
- https://doi.org/10.1021/acs.orglett.5c02157
- Citations
- 3
- Primary Topic
- Click Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- National Natural Science Foundation of China
- Yunnan Provincial Science and Technology Department
- Engineering and Physical Sciences Research Council