This review focuses on the utilization of indium(iii) as π-acid for the activation of C-C unsaturated bonds in organic synthesis. In addition to its well-known σ-coordination with carbonyl derivatives, indium(iii) undergoes efficient π-coordination with unsaturated systems to trigger nucleophilic addition. Accordingly, indium(iii) halides and salts (InX3, X = Cl, Br, I, OTf, ONf, NTf2) have been reported as useful catalysts for a broad range of carbon-carbon and carbon-heteroatom bond formation reactions, including hydrofunctionalization (hydroarylation, hydroamination, hydroalkoxylation, and hydrothiolation), enyne cycloisomerization, and related reactions. In these reactions the counterion has a significant effect on the catalytic activity, and the development of novel In(iii) complexes and the generation of highly electrophilic cationic indium(iii) species has increased its synthetic applications as a π-acid catalyst.
The RESCCUE Project is an H2020 research project that aims to help cities around the world to become more resilient to physical, social, and economic challenges, using the water sector as the central point of the approach. RESCCUE will generate models and tools to bring this objective to practice, while delivering a framework enabling city resilience assessment, planning and management. This will be achieved by integrating software tools, methods, and new knowledge related to the detailed urban services performance into novel and promising loosely coupled models (integrated models), multi-risk assessment method, and a comprehensive resilience platform. These tools will allow urban resilience assessment from a multisectorial approach, for current and future climate change scenarios, including multiple hazards and cascading effects. The RESCCUE approach will be implemented in three EU cities (Barcelona, Bristol, and Lisbon) and, with the support of UN-Habitat, disseminate their results among other cities belonging to major international networks. The aim of this paper is to present the main goals of this project, as well as the approach followed and the main expected results after the four years of implementation, so other cities around the world can use the RESCCUE approach to increase their resilience.
Indium(III) halides catalyze efficiently the intramolecular hydroarylation (IMHA) of aryl propargyl ethers. The reaction proceeds regioselectively with terminal and internal alkynes bearing electron-rich and electron-deficient substituents in the benzenes and alkynes affording only the 6-endo dig cyclization product. Additionally, a sequential indium-catalyzed IMHA and palladium-catalyzed Sonogashira coupling can be performed in one reaction vessel. Experiments with deuterium support a mechanism through electrophilic aromatic substitution.
A series of donor−acceptor−acceptor (D−A− A) and donor−acceptor−donor (D−A−D) systems based on a pyrimidine π-spacer with various substituents at the C-2 position has been successfully prepared. The synthesis involved site-selective palladium cross-coupling reactions of chloropyrimidines with triorganoindium reagents and proceed in good yields and with atom economy. 4-(N,N-Diphenylamino)phenyl was chosen as the donor group and thien-2-yl dicyanovinylene as the acceptor one. The optical, vibrational, electrochemical, and density functional theory (DFT) calculations of these molecular systems were analyzed, and experimental values show the important role of the substituents at the C-2 position of the pyrimidine with stronger electron accepting ability, absorption in a wide range of UV/vis, acceptable fluorescence lifetime, and effective intramolecular charge transfer (ICT) properties. The ICT was observed in both series by the bathochromic shift on increasing the polarity of the solvent. In addition, DFT calculations found lower lowest unoccupied molecular orbitals of D−A−A molecules that suggest good electron ejection and transportation, being good properties for their application in various organic optoelectronic devices.
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