title: 1-(N-acylamino)alkyl sulfones from N-acyl-α-amino acids or N-alkylamides.
abstract: A variety of N-(1-methoxyalkyl)amides or carbamates react readily with sodium aryl sulfinates in the presence of triphenylphosphonium tetrafluoroborate or bromide in CHCl3 under mild conditions to give 1-(N-acylamino)alkyl sulfones in good yields. A combination of this reaction with the recently described electrochemical decarboxylative α-methoxylation of N-acyl-α-amino acids to give N-(1-methoxyalkyl)amides in the presence of 3-(1-piperidino)propyl-functionalized silica gel (SiO2-Pip) enables an effective two-pot transformation of N-acyl-α-amino acids to 1-(N-acylamino)alkyl sulfones. Alternatively, N-(1-methoxyalkyl)amides can be obtained by electrochemical α-methoxylation of either N-alkylamides, lactams, or N-alkylcarbamates.
authors.affiliation: Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology , B. Krzywoustego 4, 44-100 Gliwice, Poland.
authors.forename: Jakub
authors.initials: J
authors.lastname: Adamek
authors.forename: Roman
authors.initials: R
authors.lastname: Mazurkiewicz
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Październiok-Holewa
authors.forename: Mirosława
authors.initials: M
authors.lastname: Grymel
authors.forename: Anna
authors.initials: A
authors.lastname: Kuźnik
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Zielińska
mesh_terms: D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D015394:Molecular Structure; D058428:Silica Gel / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry*
chemical_list: D000577:Amides; D000596:Amino Acids; D002219:Carbamates; D013438:Sulfhydryl Compounds; D013450:Sulfones; D058428:Silica Gel