Herein, we describe a novel photoinduced iron-catalyzed strategy for multicomponent C-H alkylation of in situ generated imines. By utilizing the alkyl radicals generated through iron-mediated photocatalytic C-H activation, the imines formed in situ are further subjected to addition reactions, resulting in the synthesis of various secondary and tertiary amine products. This method is simple to operate and does not require additional oxidants. It is applicable to inert alkane substrates such as cyclic alkanes, cyclic ethers, toluene, and ketones. The reaction is also compatible with various aromatic amines, alkyl amines, halogenated aromatic amines, as well as aromatic aldehydes, alkyl aldehydes, and cinnamaldehyde, among other different types of aldehydes.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.4c01986 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A novel efficient liquefaction process for corn starch through ternary deep eutectic solvent: Products characterization and liquefaction mechanism.
Int J Biol Macromol
December 2024
College of Biomass Science and Engineering, Sichuan University, Chengdu 610065, China; Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu 610065, China. Electronic address:
A novel approach for the solvothermal liquefaction of corn starch (CS) was investigated, using ternary deep eutectic solvent (TDES) as both an acidic catalyst and a source of liquefaction reagent. Synergistic effects from multi-component TDES were observed, leading to milder reaction conditions (110 °C, 35 min) and improved product selectivity (relative content of polyhydroxy compounds up to 97.83 %).
View Article and Find Full Text PDFMolecular-Oxygen-Mediated Multicomponent Oxidative Cyclization: Synthesis of Tertiary-Alcohol-Unit-Bearing -Heterocycles via Transforming C-H to C-OH Bonds.
Org Lett
December 2024
Institute of Advanced Studies and School of Pharmaceutical Sciences, Taizhou University, Jiaojiang, Zhejiang 318000, China.
We developed a molecular-oxygen-mediated multicomponent oxidative cyclization strategy to synthesize -heterocycles containing tertiary alcohol units via the formation of key C-OH bonds and quaternary carbon centers. This formal [3 + 2 + 1] annulation offers a green and sustainable alternative for the C-OH bond formation, using O as both the oxidant and oxygen source under metal- and catalyst-free conditions. Notably, continuous [1,5]-hydrogen transfer together with excess alcohols promotes the formation of C-OH-bearing products.
View Article and Find Full Text PDFAn Air-Stable, Single-Component Iridium Precatalyst for the Borylation of C-H Bonds on Large to Miniaturized Scales.
J Am Chem Soc
November 2024
Department of Chemistry, University of California Berkeley, Berkeley, California 94720, United States.
The functionalization of C-H bonds enables the modification of complex molecules, often with the intention of forming compound libraries. The borylation of aryl C-H bonds is a widely used class of C-H bond functionalization, and conventional catalyst systems for the borylation of C-H bonds consist of an iridium source and an ,-ligand, in conjunction with pinacolborane, to form the active iridium(III) tris(boryl) catalyst. These multicomponent catalyst systems complicate borylation reactions at large and small scales, due to the air sensitivity of the most common iridium precursor [Ir(cod)OMe], and, particularly on small scale, the challenges associated with dispensing multiple components with differing solubilities or that are air-sensitive.
View Article and Find Full Text PDFA Multicomponent [2+2+1] Cascade Cyclization to Synthesize Thiazol-2(3)-one.
J Org Chem
December 2024
Key Laboratory of Chemistry in Ethnic Medicinal Resources, Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicinal Endophytes, School of Ethnic Medicine, Yunnan Minzu University, Kunming, 650500, China.
A multicomponent [2+2+1] tandem cyclization of alkynones with amines and water using potassium thiocyanate as electrolyte and raw material to access thiazol-2(3)-ones has been developed. This transformation proceeded smoothly via electrocatalytic oxidative C-H bond thiolation, and nucleophilic cascade cyclization to build the (C-S/C-N) bonds to construct the C-O bond. The reaction avoided using transition metal catalysts or oxidation reagents, making it more sustainable and renewable.
View Article and Find Full Text PDFL-Proline catalyzed multi-component synthesis of -pyridyl-tetrahydroisoquinolines and their α-C(sp)-H oxygenation.
Org Biomol Chem
November 2024
Department of Applied Sciences, GUIST, Gauhati University, Guwahati-781014, Assam, India.
Herein, we report an effective multi-component synthesis that starts with readily available starting materials and accesses poly-substituted pyridine derivatives by using L-proline as a benign catalyst. This process uses cyclic amines, aldehydes, and malononitrile in a condensation reaction to produce a variety of pyridine derivatives under mild conditions. Furthermore, depending on the catalysts used, the selective synthesis of an amide and/or an aldehyde functionality is achieved through α-C(sp)-H oxygenation of the tertiary amine moiety in the resultant pyridine derivatives.
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!