The indoline skeleton is an ubiquitous scaffold found in a range of biologically active alkaloid and pharmaceutically active compounds. Indolines have also been successfully employed as chiral auxiliaries in asymmetric synthesis.1-2 On the other hand indolines are also useful for various application ranging from dyes, dye sensitized solar cell, to fuel cell (H2 storage).3 Our research group is always interested in heterocyclic systems synthesis and to this goal Pd-catalyzed reactions have been extensively studied.4 Among the known Pd-catalyzed reactions typologies Heck reaction, Buchwald-Hartwig reaction, oxidative coupling, arylation have been reported previously by our research group. In particular the amination reaction are nowadays one of the most powerful tool to obtain C-N bond formation.5-8 The evolution of this reaction was toward the use of weak bases in order to leave intact other functional groups. The further evolution was addressed to improve yield and applicability, and this goal was achieved using different ligands and through their optimization. Today we try to further enlarge the applicability and to use environmental friendly procedures. Last but not least we try to develop economic and scalable synthesis to switch the use of this reactions from research to industry. We present here a new kind of solvent “QUASI-free” reaction, combined with the use of a commercially available ligand and the use of a weak and cheap base, K2CO3. Irradiation by microwaves is the other key feature of this protocol.
|Titolo:||New environmental friendly N-aryl indolines synthesis through C-N bond formation|
BECCALLI, EGLE MARIA (Primo)
BASOLO, LUCA (Ultimo)
|Data di pubblicazione:||set-2010|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Citazione:||New environmental friendly N-aryl indolines synthesis through C-N bond formation / E. Beccalli, L. Basolo. ((Intervento presentato al convegno Ischia advanced School of Organic Chemistry tenutosi a Ischia nel 2010.|
|Appare nelle tipologie:||14 - Intervento a convegno non pubblicato|