A facile benzylic alkylation of indenes and other arenes was developed from readily available primary and secondary alcohols using our newly investigated CCC pincer Ir catalyst (SNIr-H). Excellent regioselectivity and yield (89 %) of the C3-alkylated indenes were obtained. Additionally, the challenging sp C-alkylation was readily accomplished. This method could be utilized for the synthesis of the analogs of a histamine H1 receptor antagonist and the functional material template molecule, indeno[2,1-a]indene. A hemilabile Ir -dihydride intermediate was proposed based on control experiments and previous density functional theory (DFT) calculations for the borrowing hydrogen mechanism and is key to the success of this Ir catalyst in the reduction of unactivated multi-substituted olefin intermediates.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.202206446 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A Knowledge-Based Molecular Single-Source Precursor Approach to Nickel Chalcogenide Precatalysts for Electrocatalytic Water, Alcohol, and Aldehyde Oxidations.
ACS Nano
December 2024
Department of Chemistry: Metalorganics and Inorganic Materials, Technische Universität Berlin, Straße des 17. Juni 115, Sekr. C2, Berlin 10623, Germany.
The development and comprehensive understanding of nickel chalcogenides are critical since they constitute a class of efficient electro(pre)catalysts for the oxygen evolution reaction (OER) and value-added organic oxidations. This study introduces a knowledge-based facile approach to analogous NiE (E = S, Se, Te) phases, originating from molecular β-diketiminato [NiE] complexes and their application for OER and organic oxidations. The recorded activity trends for both target reactions follow the order NiSe > NiS > NiTe.
View Article and Find Full Text PDFCopper(I)-Catalyzed Enantioselective α-Alkylation of 2-Acylimidazoles.
J Am Chem Soc
December 2024
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Catalytic asymmetric α-alkylation of simple carboxylic acid derivatives is a challenging issue due to the difficulties in achieving high catalytic efficiency and controlling the enantioselectivity. Herein, by using a copper(I)-()-DTBM-SEGPHOS complex as a catalyst and 2-acylimidazoles as pronucleophiles, a general method for the catalytic asymmetric α-alkylation of simple carboxylic acid derivatives is accomplished. Various alkyl electrophiles, including allyl bromides, benzyl bromides, propargyl bromide, and unactivated alkyl sulfonates, serve as efficient alkylation reagents.
View Article and Find Full Text PDFVisible Light-Mediated [4+2] Annulation of Silylimines with Olefins to 1-Aminotetralins Enabled by Diradical Hydrogen Atom Transfer of C-H Bonds.
Angew Chem Int Ed Engl
November 2024
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing, 401331, P. R. China.
A facile photochemical, one-pot synthesis of highly functionalized 1-aminotetralins derivatives (>70 examples) from readily accessible o-alkyl and o-formyl aryl silylimines with olefins is described. A diradical-mediated hydrogen atom transfer (DHAT) of primary, secondary, and tertiary C(sp)-H bonds of o-alkyl arylsilylimines and C(sp)-H bonds of o-formyl arylsilylimines enabled a [4+2] annulation with olefins in excellent diastereoselectivity. This was accomplished upon irradiation at λ = 420 nm in the presence of thioxanthen-9-one (10 mol %) as the sensitizer via energy transfer.
View Article and Find Full Text PDFMolecular-level Modulation of N, S-Co-Doped Mesoporous Carbon Nanospheres for Selective Aqueous Catalytic Oxidation of Ethylbenzene.
Angew Chem Int Ed Engl
November 2024
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun, Jilin, 130012, China.
Selective oxidation of aromatic alkanes into high value-added products through benzylic C-H bond activation is one of the main reactions in chemical industry. On account of the constantly increasing demand for mass production, efficient, eco-friendly and sustainable catalysts are urgently needed. Herein, we describe a facile and versatile emulsion-assisted interface self-assembly strategy towards molecular-level fabrication of co-doped mesoporous carbon nanospheres with controllable active N and S species.
View Article and Find Full Text PDFStructurally Diverse Nitrogen-Rich Scaffolds via Continuous Photo-Click Reactions.
Org Lett
December 2024
School of Chemistry, University College Dublin, O'Brien Centre for Science, Belfield, Dublin 4, Ireland.
Continuous flow technology was exploited for the effective generation of nitrile imines via photolysis of substituted aryl tetrazoles. The resulting photo-click process rapidly affords advanced nitrogen-rich scaffolds upon the subsequent trapping of the reactive dipole with alkenes, alkynes, and benzylic amines. Crucially, this approach uncovers the differential reactivity for ether vs amine tethers, thus providing facile and scalable access to underexplored medicinally relevant heterocyclic entities.
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!