Solvent‐Free, Microwave‐Assisted N‐Arylation of Indolines by using Low Palladium Catalyst Loadings

Abstract

Indoline-based compounds are abundant in nature, and the indoline skeleton is an often-encountered scaffold in a range of biologically active alkaloids, pharmaceutically active compounds, and functional molecules (e.g., sensitizers for solar cells). The wide range of uses warrants further interest in the structural modification of this class of compounds. A series of substituted N-aryl indolines is prepared by a solvent-free, palladium-catalyzed procedure. The procedure requires only low loadings of catalyst, uses microwave irradiation, and starts from commercially available substrates. The method proceeds in good yields and in short reaction times with aryl bromides, chlorides, and iodides, also on 2-substituted indolines. The combination of solvent-free methods with microwave heating will further increase in importance in the search for more environmentally acceptable synthesis methods.

Buchwald–Hartwig Amination of (Hetero)aryl Chlorides by Employing Mor‐DalPhos under Aqueous and Solvent‐Free Conditions

“…Such protocols are attractive, not only in terms of advancing green chemistry concepts, but also in terms of allowing for the possible application of a wider range of bases in such catalytic chemistry compared with reactions conducted under aqueous conditions. Noteworthy reports in this area include the work of Yoshifuji and co‐workers,17 who described the application of a Pd precatalyst featuring a diphosphanylidenecyclobutene ancillary ligand for use in the solvent‐free amination of aryl bromides at room temperature, as well as the work of Beccalli and co‐workers,18 who reported the use of solvent‐free BHA methods with microwave heating for the preparation of a series of substituted N ‐arylindolines by employing aryl bromides, chlorides, and iodides.…”

Design for carbon–carbon bond forming reactions under ambient conditions

“…8,36,[290][291][292][293][294][295][296] In recent years, mechanochemistry (i.e. 8,36,[290][291][292][293][294][295][296] In recent years, mechanochemistry (i.e.…”

Creation of DABCO‐Based Amphoteric Ionic Liquid Supported TiO2 Nanoparticles: Execution of Amplified Catalytic Properties on Microwave‐Assisted Synthesis of N‐Substituted Pyrroles

“…The traditional heating required 3–9 times additional energy than the microwave assisted organic synthesis (MAOS) . Additionally microwave‐assisted reactions performed at an optimized reaction temperature found to be cleaner and also lead to less by‐products …”