Metal-Free Addition of Benzyl Halides to Aldehydes Using Super Electron Donors: Access to 3,4-Dihydroisocoumarins and 1,2-Diarylethanols
- 23 November 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (23), 15736-15742
- https://doi.org/10.1021/acs.joc.0c02374
Abstract
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.Funding Information
- Aix-Marseille Universit?
- Centre National de la Recherche Scientifique
This publication has 34 references indexed in Scilit:
- Calcium(II)- and Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in HexafluoroisopropanolOrganic Letters, 2019
- Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acidsChemical Communications, 2018
- First TDAE Reactivity Using Benzonitrile Derivatives as Substrates and Its Application to the Synthesis of 3-Substituted Isochroman-1-onesSynthesis, 2018
- Cobalt‐Catalyzed Coupling of Benzoic Acid C−H Bonds with Alkynes, Styrenes, and 1,3‐DienesAngewandte Chemie International Edition, 2018
- Synthesis, antiproliferative activities, and computational evaluation of novel isocoumarin and 3,4-dihydroisocoumarin derivativesEuropean Journal of Medicinal Chemistry, 2016
- An Enantioselective Approach toward 3,4-Dihydroisocoumarin through the Bromocyclization of Styrene-type Carboxylic AcidsThe Journal of Organic Chemistry, 2011
- Therapeutic potential of resveratrol: the in vivo evidenceNature Reviews Drug Discovery, 2006
- Combretastatins: from natural products to drug discoveryNatural Product Reports, 2003
- Original reaction of p-nitrobenzyl chloride with aldehydes using tetrakis(dimethylamino)ethylene (TDAE)Tetrahedron Letters, 2003
- Antimalarial Dihydroisocoumarins Produced by Geotrichum sp., an Endophytic Fungus of Crassocephalum crepidioidesJournal of Natural Products, 2003