Access to Carbonyl Azides via Iodine(III)-Mediated Cross-Coupling
Herein, we present a prominent metal-free C-N cross-coupling platform that enables access to carbamoyl- and ketoazides from isocyanides or silyl enol ethers and trimethylsilyl azide (TMSN<sub>3</sub>) with an aid of iodine(III) promoter. This offers a rapid route to a diverse set of synthetically valuable azide decorated fragments with excellent substrate scope and good to excellent yields. The disclosed platform exemplifies the use of TMSN<sub>3</sub> for incorporation of the azide fragment without the loss of N<sub>2</sub>.
Authors
- Li Xu
- Qing Yan (ORCID: https://orcid.org/0000-0002-9386-9711)
- Lanlan Lv
- Gregory R. Alvey (ORCID: https://orcid.org/0009-0006-2467-5338)
- Markus D. Kärkäs (ORCID: https://orcid.org/0000-0002-6089-5454)
- Xiang‐Shan Wang (ORCID: https://orcid.org/0000-0002-0077-7819)
- Andrey Shatskiy (ORCID: https://orcid.org/0000-0002-7249-7437)
- Elena V. Stepanova (ORCID: https://orcid.org/0000-0001-9617-9110)
Institutions
- Jiangsu Normal University (CN)
- National Research Tomsk State University (RU)
- Tomsk Polytechnic University (RU)
- KTH Royal Institute of Technology (SE)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-17
- DOI
- https://doi.org/10.1021/acs.orglett.4c03212
- Citations
- 2
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- Jiangsu Normal University
- Stiftelsen Olle Engkvist Byggmästare
- Kungliga Tekniska Högskolan
- Vetenskapsrådet
- Magnus Bergvalls Stiftelse
- Ministry of Science and Higher Education of the Russian Federation