Transfer of electrophilic NH using convenient sources of ammonia:
direct synthesis of N–H sulfoximines from sulfoxides
direct synthesis of N–H sulfoximines from sulfoxides
File(s)
OA Location
Author(s)
Zenzola, M
Doran, R
Degennaro, L
Luisi, R
Bull, JA
Type
Journal Article
Abstract
The transfer of nitrogen atoms is extremely valuable in the preparation of medicinal compounds. Here, a new system for NH transfer is developed to prepare sulfoximines, which are emerging as valuable motifs for drug discovery. This is achieved using readily available sources of nitrogen without the requirement for pre-activation or for metal catalysts in an operationally simple protocol. Mixing ammonium salts with diacetoxyiodobenzene in a choice of solvents directly converts sulfoxides to sulfoximines. The protocol is tolerant of many other functional groups and heterocycles that are important in drug compounds. This is the first example of the use of ammonia sources with diacetoxyiodobenzene providing a source of electrophilic nitrogen. Control and mechanistic studies suggest a short-lived electrophilic intermediate, likely to be PhINH or PhIN+.
Date Issued
2016-06-13
Date Acceptance
2016-03-22
Citation
Angewandte Chemie - International Edition, 2016, 55 (25), pp.7203-7207
ISSN
1433-7851
Publisher
Wiley
Start Page
7203
End Page
7207
Journal / Book Title
Angewandte Chemie - International Edition
Volume
55
Issue
25
License URL
Sponsor
The Royal Society
Engineering & Physical Science Research Council (E
Engineering & Physical Science Research Council (EPSRC)
Identifier
https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201602320
Grant Number
UF140161
EP/K503733/1
EP/J001538/1
Subjects
Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
hypervalent compounds
nitrogen
reactive intermediates
sulfur
synthetic methods
HYPERVALENT IODINE(III) REAGENTS
CATALYZED NITRENE TRANSFER
MEDICINAL CHEMISTRY
ROBUSTNESS SCREEN
AMINATION
BOND
SULFIMIDES
IMINATION
SULFIDES
OLEFINS
hypervalent compounds
nitrogen
reactive intermediates
sulfur
synthetic methods
Organic Chemistry
03 Chemical Sciences
Publication Status
Published
Date Publish Online
2016-04-29