Tropone-Enabled Pd-Catalyzed C(sp<sup>2</sup>)–H Functionalization of Phenylalanine: Switchable Access to Indoline and Olefinate
Herein, we report Pd-catalyzed and site-selective C(sp<sup>2</sup>)-H amination/olefination of phenylalanine. The transformation proceeds via a <i>troponyl</i> carbonyl-directed intramolecular C-N cyclization forming indoline scaffolds through C(sp<sup>2</sup>)-H activation with PIDA. In the absence of PIDA, <i>ortho</i>-C(sp<sup>2</sup>)-H olefination occurs at phenylalanine. This method shows broad substrate scope and excellent functional group tolerance, providing a versatile tool for peptide diversification.
Authors
- Swati Nayak (ORCID: https://orcid.org/0000-0002-3597-3772)
- Akash Patnaik (ORCID: https://orcid.org/0000-0001-5306-0208)
- Nagendra K. Sharma (ORCID: https://orcid.org/0000-0003-0901-0523)
- Chinmay K. Jena
Institutions
- National Institute of Science Education and Research (IN)
- Homi Bhabha National Institute (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-09-22
- DOI
- https://doi.org/10.1021/acs.orglett.5c03211
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00