Ligand-Controlled C2- or C3-Selectivity Switching in the Palladium-Catalyzed C-H Arylation of Nonsubstituted 1 H-Pyrrole

Org Lett. 2025 Jan 10;27(1):141-146. doi: 10.1021/acs.orglett.4c04085. Epub 2024 Dec 30.

Abstract

The C2- or C3-selective direct C-H arylation of nonsubstituted 1H-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 1H-pyrrole was realized for the first time. tBuOLi played an important role in suppressing N-arylation and accelerating C2- or C3-arylation.