Pd(II)-Catalyzed meta-C–H Olefination, Arylation, and Acetoxylation of Indolines Using a U-Shaped Template
- Authors
- Type
- Published Article
- Journal
- Journal of the American Chemical Society
- Publisher
- American Chemical Society
- Publication Date
- Jul 13, 2014
- Volume
- 136
- Issue
- 30
- Pages
- 10807–10813
- Identifiers
- DOI: 10.1021/ja505737x
- PMID: 25007097
- Source
- CCHF
- License
- White
Abstract
meta-C-H olefination, arylation, and acetoxylation of indolines have been developed using nitrile-containing templates. The combination of a monoprotected amino acid ligand and the nitrile template attached at the indolinyl nitrogen via a sulfonamide linkage is crucial for the meta-selective C-H functionalization of electron-rich indolines that are otherwise highly reactive toward electrophilic palladation at the para-positions. A wide range of synthetically important and advanced indoline analogues are selectively functionalized at the meta-positions.