This report discloses a novel Pd-catalyzed sequential three-component multiple reaction of alkenes, bromoalkynes, and boronic acids using alkenes as hydride and alkenyl donors, leading to highly stereoselective assembly of (,)-1,3-diene derivatives. Mechanistic studies demonstrate that the generation and reutilization of palladium hydride species are critical to the success of this transformation. In addition, the good functional group compatibility, late-stage modification, and investigation of photophysical properties of 1,3-diene products illustrate the synthetic value of this strategy.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.2c01406 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Dirhodium-Palladium Dual-Catalyzed [1 + 1 + 3] Annulation to Heterocycles Using Primary Amines or HO as the Heteroatom Sources.
J Am Chem Soc
January 2025
State Key Laboratory of Organometallic Chemistry and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
The ever-increasing demand in chemical biology and medicinal research requires the development of new synthetic methods for the rapid construction of libraries of heterocycles from simple raw materials. In this context, the utilization of primary amines or HO as the simple - or -sources in the assembly of a heterocyclic ring skeleton is highly desirable from the viewpoint of atom- and step-economy. Herein, we describe a highly efficient three-component reaction of diazo, allylic diacetates, and commercially available anilines (or HO) to access structurally diverse pyrrolidine and tetrahydrofuran derivatives.
View Article and Find Full Text PDFHigh Molecular Weight Uniform Polymers Encoding Octal Sequences by Passerini Iterative Exponential Growth.
J Am Chem Soc
January 2025
Department of Chemistry, Seoul National University, Seoul 08826, Korea.
Sequence-defined polymers composed of a large pool of chemically distinct monomers (SDPs) have been pursued to achieve the structural and functional precisions exhibited by biopolymers in nonbiological environments. In contrast to the incremental growth of SDPs by sequential addition of individual monomers, the iterative exponential growth (IEG) method allows the synthesis of high molecular-weight SDPs, but their sequences have been composed mostly of binary monomers. Consequently, achieving high molecular-weight SDPs built with a large pool of monomers remains a challenge.
View Article and Find Full Text PDFSequential Photocatalysis for Homologative Diversification of α-Amino Acids to β-Amino Acids Via Phosphonium Ylide Linchpin Strategy.
J Am Chem Soc
December 2024
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo, Kyoto 606-8501, Japan.
β-Amino acids serve as crucial building blocks for a broad range of biologically active molecules and peptides with potential as peptidomimetics. While numerous methods have been developed for the synthesis of β-amino acids, most of them require multistep preparation of specific reagents and substrates, which limits their synthetic practicality. In this regard, a homologative transformation of abundant and readily available α-amino acids would be an attractive approach for β-amino acid synthesis.
View Article and Find Full Text PDFControllable Phosphine-Catalyzed Three-Component Domino Reaction of Activated Alkenes with Morita-Baylis-Hillman (MBH) Carbonates: Divergent Synthesis of Densely Functionalized Cyclopentanes and Diquinanes.
Org Lett
December 2024
Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002, China.
An unexpected phosphine-catalyzed controllable three-component domino reaction involving [1 + 2 + 2] annulation and [1 + 2 + 2]/[3 + 2] sequential annulation reaction of 2-arylmethylidene cyanoacetates/malononitriles with Morita-Baylis-Hillman (MBH) carbonates has been developed. A broad range of densely functionalized cyclopentanes and diquinanes bearing five or four consecutive stereogenic centers, including two all-carbon quaternary stereocenters, were smoothly acquired in moderate to excellent yields under mild reaction conditions from readily available materials. Moreover, this divergent transformation enables the simultaneous generation of three or four new C-C bonds and one or two carbocyclic rings in only one step.
View Article and Find Full Text PDFSBA-Pr-IS-MN-DM: a new fluorescent chemosensor for trace detection of silver in aqueous solutions.
Sci Rep
November 2024
Centre of Excellence for Research in Sustainable Chemistry, Department of Chemistry, Federal University of São Carlos, São Carlos, 13565-905, SP, Brazil.
Initially, SBA-Propyl-Isatin-Malononitrile (SBA-Pr-IS-MN) was prepared by the reaction of SBA-Pr-Cl with IS-MN, which was synthesized by the reaction of isatin and malononitrile. This organic and inorganic hybrid material can be functionalized by the sequential reaction with dimedone to obtain the target product SBA-Pr-Is-MN-DM, which was investigated as a chemosensor by fluorescence spectroscopy to detect trace amount of Ag among several other cations in aqueous media.
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!