Highly chemoselective NH- and O-transfer to thiols using hypervalent iodine reagents: synthesis of sulfonimidates and sulfonamides
File(s)
Supporting information
Accepted version
Author(s)
Type
Journal Article
Abstract
Aryl thiols can be selectively converted to sulfonimidates or sulfonamides with 3 new S–X connections being made selectively in one-pot. Using hypervalent iodine reagents in the presence of ammonium carbamate, NH- and O-groups are transferred under mild and practical conditions. Reducing the loading of ammonium carbamate changed the product distribution, converting the sulfonimidate to the sulfonamide. Studies into the possible intermediate species are presented, suggesting that multiple pathways may be possible via sulfinate esters, or related intermediates, with each species forming the same products.
Date Issued
2018-04-13
Date Acceptance
2018-04-11
Citation
Organic Letters, 2018, 20 (9), pp.2599-2602
ISSN
1523-7052
Publisher
American Chemical Society
Start Page
2599
End Page
2602
Journal / Book Title
Organic Letters
Volume
20
Issue
9
Copyright Statement
© 2018 American Chemical Society
Sponsor
Engineering & Physical Science Research Council (EPSRC)
Engineering & Physical Science Research Council (E
The Royal Society
Identifier
https://pubs.acs.org/doi/10.1021/acs.orglett.8b00788
Grant Number
EP/J001538/1
EP/K503733/1
UF140161
Subjects
03 Chemical Sciences
Organic Chemistry
Publication Status
Published