Ligand-Controlled C2- or C3-Selectivity Switching in the Palladium-Catalyzed C–H Arylation of Nonsubstituted 1<i>H</i>-Pyrrole
The C2- or C3-selective direct C-H arylation of nonsubstituted 1<i>H</i>-pyrrole with aryl chlorides/nonaflates was achieved using catalysts derived from palladium and appropriate phosphine ligands. The site selectivity of the arylation can be switched by changing the ligands, and the C3-selective arylation of nonsubstituted 1<i>H</i>-pyrrole was realized for the first time. <i>t</i>BuOLi played an important role in suppressing N-arylation and accelerating C2- or C3-arylation.
Authors
- Miyuki Yamaguchi
- Sakiko Fujiwara
- Kei Manabe (ORCID: https://orcid.org/0000-0002-9759-1526)
- Kengo Morioka
- Hideyuki Konishi (ORCID: https://orcid.org/0000-0003-0519-0117)
- Kazutaka Nakai
- Ayano Sato
Institutions
- University of Shizuoka (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-30
- DOI
- https://doi.org/10.1021/acs.orglett.4c04085
- Citations
- 3
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.75
Funders
- Japan Agency for Medical Research and Development
- Hamamatsu Foundation for Science and Technology Promotion
- Tokyo Ohka Foundation for The Promotion of Science and Technology
- Japan Society for the Promotion of Science