[reaction: see text] Iron(III) chloride-catalyzed effective allylation reactions of acetals with allyltrimethylsilane proceeded smoothly in high to excellent yields. In addition, this method could be applied to the one-pot synthesis of homoallyl benzyl ethers by a combination of dibenzyl acetalization of aldehydes and consecutive allylation of dibenzyl acetals.
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Org Lett
July 2022
Department of Chemistry & Chemical Biology, Indiana University-Purdue University Indianapolis, Indianapolis, Indiana 46202, United States.
A photoinduced, iron(III) chloride-catalyzed C-H activation of -methyl amides and ethers leads to the formation of C-S and C-Se bonds via a ligand-to-metal charge transfer (LMCT) process. This methodology converts secondary and tertiary amides, sulfonamides, and carbamates into the corresponding amido--acetal derivatives in good yields. Mechanistic work revealed that this transformation proceeds through a hydrogen atom transfer (HAT) involving chlorine radical intermediates.
View Article and Find Full Text PDFMolecules
February 2020
Research Centre in Synthesis and Catalysis, Department of Chemical Science, University of Johannesburg, PO Box 524, Auckland Park 2006, South Africa.
Amide functional groups are prominent in a broad range of organic compounds with diverse beneficial applications. In this work, we report the synthesis of these functional groups via an iron(iii) chloride-catalyzed direct amidation of esters. The reactions are conducted under solvent-free conditions and found to be compatible with a range of amine and ester substrates generating the desired amides in short reaction times and good to excellent yields at a catalyst loading of 15 mol%
View Article and Find Full Text PDFOrg Biomol Chem
December 2018
Department of Chemistry and Biochemistry, University of Missouri - St Louis, One University Boulevard, St Louis, Missouri 63121, USA.
Glycosyl chlorides have historically been activated using harsh conditions and/or toxic stoichiometric promoters. More recently, the Ye and the Jacobsen groups showed that glycosyl chlorides can be activated under organocatalytic conditions. However, those reactions are slow, require specialized catalysts and high temperatures, but still provide only moderate yields.
View Article and Find Full Text PDFOrg Lett
March 2016
University of Michigan , Department of Chemistry, Willard Henry Dow Laboratory, 930 North University Avenue, Ann Arbor, Michigan 48109, United States.
A mild, catalytic method for the synthesis of 3,4-dihydro-2H-pyrans is described. The FeCl3-catalyzed transformation of aryl- and alkyl β-diketones enables synthetic access to functionalized pyran core structures incorporated in many natural products and biologically active target structures. The method represents a mild alternative to currently available reaction protocols relying on stoichiometric reagents and harsh reaction conditions.
View Article and Find Full Text PDFJ Org Chem
September 2014
Instituto de Química Rosario-CONICET, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario , Suipacha 531, 2000 Rosario, Santa Fe, Argentina.
Iron(III) chloride-catalyzed cyclopentannulation of π-conjugated 1,3-dicarbonyl compounds is described. An interrupted vinylogous iso-Nazarov reaction of trienones was established in which cyclopenta[b]furan derivatives are obtained as single diastereomers.
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