Metal-Free Addition of Benzyl Halides to Aldehydes Using Super Electron Donors: Access to 3,4-Dihydroisocoumarins and 1,2-Diarylethanols.

J Org Chem

Aix Marseille Univ, CNRS, ICR UMR CNRS 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS 30064, Cedex 05 13385 Marseille, France.

Published: December 2020

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.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.0c02374DOI Listing

Publication Analysis

Top Keywords

metal-free addition
8
benzyl halides
8
halides aldehydes
8
aldehydes super
8
super electron
8
34-dihydroisocoumarins 12-diarylethanols
8
addition benzyl
4
electron donors
4
donors access
4
access 34-dihydroisocoumarins
4

Similar Publications

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 PDF

Oxygen, light, and mechanical force mediated radical polymerization toward precision polymer synthesis.

Chem 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 PDF

Innovative perspectives on metal free contrast agents for MRI: Enhancing imaging efficacy, and AI-driven future diagnostics.

Acta 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 PDF

Functionalization of Pyridines at the C4 Position via Metalation and Capture.

Angew 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 PDF

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.

View Article and Find Full Text PDF

Want 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!