Nickel complexes of chiral spiroBox ligand catalyzed Friedel-Crafts alkylation reaction of indoles with nitroalkenes. Excellent yields (up to 99%) and enantiomeric excess (ee) values (up to 97%) were obtained with a broad scope of substrates. This catalytic system provides a facile synthesis of optically active 2-indolyl-1-nitro derivatives with high yield and enantioselectivity.
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http://dx.doi.org/10.1039/d4ra08471c | DOI Listing |
RSC Adv
March 2025
College of Chemical Engineering, Qingdao University of Science and Technology Qingdao 266042 China.
Nickel complexes of chiral spiroBox ligand catalyzed Friedel-Crafts alkylation reaction of indoles with nitroalkenes. Excellent yields (up to 99%) and enantiomeric excess (ee) values (up to 97%) were obtained with a broad scope of substrates. This catalytic system provides a facile synthesis of optically active 2-indolyl-1-nitro derivatives with high yield and enantioselectivity.
View Article and Find Full Text PDFJ Org Chem
March 2025
Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India.
A simple one-pot, two-step strategy for the synthesis of three-dimensional (3D) polyheterocyclic -oxindoles by Lewis-acid-catalyzed Friedel-Crafts type -3 alkylation of indoles regioselective nucleophilic ring opening of -epoxyoxindoles, followed by -TSA-catalyzed Pictet-Spengler reaction with aldehydes in up to 98% yield and 1.4:1 diastereomeric ratio has been developed.
View Article and Find Full Text PDFChem Asian J
March 2025
Chulalongkorn University, Department of Chemistry, Faculty of Science, Phayathai Road, 10330, Bangkok, THAILAND.
This study presents a novel and practical strategy for synthesizing cannabinoids using a fluorinated alcohol solvent for the first time. Hexafluoroisopropanol (HFIP) was found to efficiently promote intermolecular Friedel-Crafts alkylation between allylic alcohols and electron-rich aromatics. This approach enabled the successful synthesis of cannabidiol (CBD) derivatives bearing various alkyl substituents, as well as the corresponding unnatural regioisomer (abnCBD), achieving moderate to high yields under mild conditions without the need for additional catalysts or other reagents.
View Article and Find Full Text PDFJ Org Chem
March 2025
Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma 74078, United States.
The torsional strain of -configured medium-sized (6-8) cycloalkenes imparts substantial potential energy efficiently toward ionic additions through generated reactive carbenium species. These reactions have been underexplored due to a historical necessity for harsh ultraviolet irradiation. We report here the Friedel-Crafts (FC) type reactivity of arylcycloalkenes (ACs) and π-nucleophiles for the first time with weak Brønsted acid and visible light energy transfer catalysis.
View Article and Find Full Text PDFOrg Lett
March 2025
Department of Chemical Sciences, Tezpur University, Napaam, Sonitpur-784028, Assam, India.
Described herein is a mild catalytic dehydrative Friedel-Crafts alkylation of 1,1-diarylalkanols─a challenging reaction with exceedingly rare previous success, presumably because of the unfavorable steric hindrance around the reactive centers and the competitive E1 reaction. Executing in an intramolecular fashion and benefiting from the high nucleophilicity of indole, we have successfully utilized this reaction in synthesizing 3,4-fused indoles. Interestingly, the Friedel-Crafts alkylation strategy could also be applied to access 4,5-fused indoles via modification of the tether connecting the alcohol and indole moieties.
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