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Controllable Skeletal and Peripheral Editing of Pyrroles with Vinylcarbenes.
- Source :
- Angewandte Chemie International Edition; 6/10/2024, Vol. 63 Issue 24, p1-11, 11p
- Publication Year :
- 2024
-
Abstract
- The skeletal editing of azaarenes through insertion, deletion, or swapping of single atoms has recently gained considerable momentum in chemical synthesis. Here, we describe a practical skeletal editing strategy using vinylcarbenes in situ generated from trifluoromethyl vinyl N‐triftosylhydrazones, leading to the first dearomative skeletal editing of pyrroles through carbon‐atom insertion. Furthermore, depending on the used catalyst and substrate, three types of peripheral editing reactions of pyrroles are also disclosed: α‐ or γ‐selective C−H insertion, and [3+2] cycloaddition. These controllable molecular editing reactions provide a powerful platform for accessing medicinally relevant CF3‐containing N‐heterocyclic frameworks, such as 2,5‐dihydropyridines, piperidines, azabicyclo[3.3.0]octadienes, and allylated pyrroles from readily available pyrroles. Mechanistic insights from experiments and density functional theory (DFT) calculations shed light on the origin of substrate‐ or catalyst‐controlled chemo‐ and regioselectivity as well as the reaction mechanism. [ABSTRACT FROM AUTHOR]
- Subjects :
- PYRROLES
DENSITY functional theory
CHEMICAL synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 63
- Issue :
- 24
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 177626774
- Full Text :
- https://doi.org/10.1002/anie.202401359