title: Redox-neutral α-sulfenylation of secondary amines: ring-fused N,S-acetals.
abstract: Secondary amines react with thiosalicylaldehydes in the presence of catalytic amounts of acetic acid to generate ring-fused N,S-acetals in redox-neutral fashion. A broad range of amines undergo α-sulfenylation, including challenging substrates such morpholine, thiomorpholine, and piperazines. Computational studies employing density functional theory indicate that acetic acid reduces the energy barriers of two separate steps, both of which involve proton transfer.
authors.affiliation: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.
authors.forename: Claire L
authors.initials: CL
authors.lastname: Jarvis
authors.forename: Matthew T
authors.initials: MT
authors.lastname: Richers
authors.forename: Martin
authors.initials: M
authors.lastname: Breugst
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
authors.forename: Daniel
authors.initials: D
authors.lastname: Seidel
mesh_terms: D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D019342:Acetic Acid / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009025:Morpholines / Q000737:chemistry; D010084:Oxidation-Reduction; D010879:Piperazines / Q000737:chemistry; D011522:Protons
chemical_list: D000080:Acetals; D000588:Amines; D009025:Morpholines; D010879:Piperazines; D011522:Protons; C028971:thiamorpholine; C037574:morpholine; D019342:Acetic Acid