title: Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides.
abstract: A new system for NH transfer is developed for the preparation of sulfoximines, which are emerging as valuable motifs for drug discovery. The protocol employs readily available sources of nitrogen without the requirement for either preactivation or for metal catalysts. Mixing ammonium salts with diacetoxyiodobenzene directly converts sulfoxides into sulfoximines. This report describes the first example of using of ammonia sources with diacetoxyiodobenzene to generate an electrophilic nitrogen center. Control and mechanistic studies suggest a short-lived electrophilic intermediate, which is likely to be PhINH or PhIN(+) .
authors.affiliation: Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ, UK.|Department of Pharmacy, Drug Sciences, University of Bari "A. Moro", Via E. Orabona 4, Bari, 70125, Italy.
authors.forename: Marina
authors.initials: M
authors.lastname: Zenzola
authors.affiliation: Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ, UK.
authors.forename: Robert
authors.initials: R
authors.lastname: Doran
authors.affiliation: Department of Pharmacy, Drug Sciences, University of Bari "A. Moro", Via E. Orabona 4, Bari, 70125, Italy.
authors.forename: Leonardo
authors.identifier: 0000-0002-2187-9419
authors.initials: L
authors.lastname: Degennaro
authors.affiliation: Department of Pharmacy, Drug Sciences, University of Bari "A. Moro", Via E. Orabona 4, Bari, 70125, Italy. renzo.luisi@uniba.it.
authors.forename: Renzo
authors.identifier: 0000-0002-9882-7908
authors.initials: R
authors.lastname: Luisi
authors.affiliation: Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ, UK. j.bull@imperial.ac.uk.
authors.forename: James A
authors.identifier: 0000-0003-3993-5818
authors.initials: JA
authors.lastname: Bull
keywords: hypervalent compounds; nitrogen; reactive intermediates; sulfur; synthetic methods