A simple and straightforward method for the synthesis of 4-iodo and 5-iodopyrrole-3-carboxaldehydes is developed from a common set of starting materials by tuning the reaction conditions. This sequential multicomponent protocol involves I-mediated regioselective C4-iodination and aromatization of intermediate dihydropyrrole, generated through proline-catalyzed direct Mannich reaction-cyclization sequence between succinaldehyde and imines, to access 4-iodopyrroles. While aerobic oxidative aromatization of dihydropyrrole to pyrrole followed by NIS-mediated regioselective iodination furnished 5-iodopyrroles in a two-pot fashion. A series of site-selective C4/C5-iodopyrroles have been synthesized in good to high yields (up to 78%) and DFT calculations of these compounds were also performed.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c9ob02501d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Asymmetric Three-Component Radical Cascade Reactions Enabled by Synergistic Photoredox/Brønsted Acid Catalysis: Access to α-Amino Acid Derivatives.
ACS Cent Sci
January 2025
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China.
Multicomponent reactions (MCRs), highly sought-after methods to produce atom-, step-, and energy-economic organic syntheses, have been developed extensively. However, catalytic asymmetric MCRs, especially those involving radical species, remain largely unexplored owing to the difficulty in stereoselectively regulating the extraordinarily high reactivity of open-shell radical species. Herein, we report a conceptually novel catalytic asymmetric three-component radical cascade reaction of readily accessible glycine esters, α-bromo carbonyl compounds and 2-vinylcyclopropyl ketones via synergistic photoredox/Brønsted acid catalysis, in which three sequential C-C (σ/π/σ) bond-forming events occurred through a radical addition/ring-opening/radical-radical coupling protocol, affording an array of valuable enantioenriched unnatural α-amino acid derivatives bearing two contiguous stereogenic centers and an alkene moiety in moderate to good yield with high diastereoselectivity, excellent enantioselectivity and good -dominated geometry under mild reaction conditions.
View Article and Find Full Text PDFGuest Segregation in Heteromeric Multicage Systems.
J Am Chem Soc
January 2025
Department of Chemistry and Chemical Biology, TU Dortmund University, Otto-Hahn Str. 6, 44227 Dortmund, Germany.
Dynamically interconvertible metallo-supramolecular multicomponent assemblies, coexisting orthogonally in solution, serve as simplified mimics for complex networks found in biological systems. Building on recent advances in controlling the nonstatistical self-assembly of heteroleptic coordination cages and heteromeric completive self-sorting, i.e.
View Article and Find Full Text PDFAtomic-Level Stoichiometry Control of Ferroelectric HfZrO Thin Films by Understanding Molecular-Level Chemical Physical Reactions.
ACS Nano
January 2025
Department of Materials Science and Engineering, Incheon National University, Incheon 22012, Korea.
HfO-based thin films have garnered significant interest for integrating robust ferroelectricity into next-generation memory and logic chips, owing to their applicability with modern Si device technology. While numerous studies have focused on enhancing ferroelectric properties and understanding their fundamentals, the fabrication of ultrathin HfO-based ferroelectric films has seldom been reported. This study presents the concept of atomic-level stoichiometry control of ferroelectric HfZrO films by examining the molecular-level interactions of precursor molecules in the atomic layer deposition (ALD) process through theoretical calculations.
View Article and Find Full Text PDFTunable Generation of Spatial Entanglement in Nonlinear Waveguide Arrays.
Phys Rev Lett
December 2024
Université Paris Cité, CNRS, Laboratoire Matériaux et Phénomènes Quantiques, 75013 Paris, France.
Harnessing high-dimensional entangled states of light presents a frontier for advancing quantum information technologies, from fundamental tests of quantum mechanics to enhanced computation and communication protocols. In this context, the spatial degree of freedom stands out as particularly suited for on-chip integration. But while traditional demonstrations produce and manipulate path-entangled states sequentially with discrete optical elements, continuously coupled nonlinear waveguide systems offer a promising alternative where photons can be generated and interfere along the entire propagation length, unveiling novel capabilities within a reduced footprint.
View Article and Find Full Text PDFSelective Ni(I)/Ni(III) Process for Consecutive Geminal C(sp)-C(sp) Bond Formation.
J Am Chem Soc
December 2024
School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China.
Ni-catalyzed multicomponent cross-couplings have emerged as a powerful strategy for efficiently constructing complex molecular architectures from a diverse array of organic halides. Despite its potential, selectively forming multiple chemical bonds in a single operation, particularly in the realm of cross-electrophile coupling catalysis, remains a significant challenge. In this study, we have developed a consecutive open-shell reductive Ni catalysis, enabling the formation of two geminal C(sp)-C(sp) bonds from two stereoelectronically similar C(sp)-I reactants in conjunction with a methylene electrophile.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!