Synthesis of NH-Sulfoximines from Sulfides by Chemoselective One-Pot N- and O-Transfers
File(s)
Accepted version
Author(s)
Type
Journal Article
Abstract
Direct synthesis of NH-sulfoximines from sulfides has been
achieved through O and NH transfer in the same reaction, occurring with complete selectivity. The reaction is mediated by bisacetoxyiodobenzene under simple conditions and employs inexpensive N-sources. Preliminary studies indicate that NH- transfer is likely to be first, followed by oxidation, but the reaction proceeds successfully in either order. A wide range of functional groups and biologically relevant compounds are tolerated. The use of AcO15NH4 affords 15N-labeled compounds.
achieved through O and NH transfer in the same reaction, occurring with complete selectivity. The reaction is mediated by bisacetoxyiodobenzene under simple conditions and employs inexpensive N-sources. Preliminary studies indicate that NH- transfer is likely to be first, followed by oxidation, but the reaction proceeds successfully in either order. A wide range of functional groups and biologically relevant compounds are tolerated. The use of AcO15NH4 affords 15N-labeled compounds.
Date Issued
2017-01-01
Date Acceptance
2016-12-01
Citation
Chemical Communications, 2017, 53, pp.348-351
ISSN
1364-548X
Publisher
Royal Society of Chemistry
Start Page
348
End Page
351
Journal / Book Title
Chemical Communications
Volume
53
Copyright Statement
© The Royal Society of Chemistry 2016.
Sponsor
Engineering & Physical Science Research Council (EPSRC)
Engineering & Physical Science Research Council
The Royal Society
Identifier
http://pubs.rsc.org/en/content/articlelanding/2016/cc/c6cc08891k#!divAbstract
Grant Number
EP/J001538/1
EP/K503733/1
UF140161
Subjects
Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
CATALYZED NITRENE TRANSFER
MEDICINAL CHEMISTRY
KINETIC RESOLUTION
SULFOXIDES
IMINATION
SULFIMIDES
AMINATION
VERSATILE
ARENES
ACYL
Organic Chemistry
03 Chemical Sciences
Publication Status
Published