We report here the intermolecular metal-free addition reaction of functionalized benzyl halides to aldehydes using a super electron donor (SED). The metal-free and mild conditions allowed the formation of 3,4-dihydroisocoumarins and 1,2-diarylethanols with unprecedented functional group tolerance.
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http://dx.doi.org/10.1021/acs.joc.0c02374 | DOI Listing |
J Org Chem
January 2025
Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
The insertion of carbene into secondary amide N-H bonds remains underexplored in organic synthesis. In this work, we discovered the visible-light-induced insertion of siloxycarbene into amide N-H bonds. This metal-free, facile reaction proceeds with atom economy under mild conditions with a broad range of secondary N-H amides, including benzanilide, acetanilide, oxindole, isatin, quinolinone, and maleimide, affording stable - and -acetals in excellent isolated yields.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200438, China.
The synthesis of polymers with well-defined composition, architecture, and functionality has long been a focal area of research in the field of polymer chemistry. The advancement of controlled radical polymerization (CRP) has facilitated the synthesis of precise polymers, which are endowed with new properties and functionalities, thereby exhibiting a wide range of applications. However, radical polymerization faces several challenges, such as oxygen intolerance, and common thermal initiation methods may lead to side reactions and depolymerization.
View Article and Find Full Text PDFActa Biomater
January 2025
Institute of Smart Biomedical Materials, School of Materials Science and Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, PR China. Electronic address:
The U.S. Food and Drug Administration (FDA) has issued a boxed warning and mandated additional safety measures for all gadolinium-based contrast agents (GBCAs) used in clinical magnetic resonance imaging (MRI) due to their prolonged retention in the body and associated adverse health effects.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Department of Chemistry, Texas A&M University, PO Box 30012, College Station, TX 77842-30012.
The functionalization of pyridines at positions remote to the N-atom remains an outstanding problem in organic synthesis. The inherent challenges associated with overriding the influence of the embedded N-atom within pyridines was overcome using n-butylsodium, which provided an avenue to deprotonate and functionalize the C4-position over traditionally observed addition products that are formed with organolithium bases. In this work, we show that freshly generated 4-sodiopyrdines could undergo transition metal free alkylation reactions directly with a variety of primary alkyl halides bearing diverse functional groups.
View Article and Find Full Text PDFLangmuir
January 2025
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
Advanced oxidation technology plays an important role in wastewater treatment due to active substances with high redox potential. Biochar is a versatile and functional biomass material. It can be used for resource management of various waste biomasses.
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