PIDA-mediated segment coupling for the synthesis of azido-methyl substituted ketones <i>via</i> 1,5-hydrogen atom transfer (HAT)
PIDA-mediated segment coupling of TMSN<sub>3</sub>, a homoallylic alcohol and an electron-deficient alkyne/alkene gives γ-azido keto ester/nitrile/phosphonate/sulfones. These metal-free transformations proceed <i>via</i> radical-mediated 1,5-HAT, followed by oxidation, to provide γ-azido keto derivatives with excellent stereoselectivity. This operationally simple three-component coupling involves the formation of C-N, C-C, C-H, and CO bonds in a single step.
Authors
- Santosh J. Gharpure (ORCID: https://orcid.org/0000-0002-6653-7236)
- Akash Khandelwal (ORCID: https://orcid.org/0000-0002-0472-7173)
- Rupali S. Chavan (ORCID: https://orcid.org/0000-0001-9041-6760)
Institutions
- Indian Institute of Technology Bombay (IN)
Publication Details
- Journal
- Chemical Communications
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5cc04895h
- Primary Topic
- Chemical Reactions and Isotopes
- Type
- article
- Field-Weighted Citation Impact
- 0.00