Altmetric

Highly chemoselective NH- and O-transfer to thiols using hypervalent iodine reagents: synthesis of sulfonimidates and sulfonamides

File Description SizeFormat 
MS Sulfonimidates OL revised.pdfAccepted version528.63 kBAdobe PDFView/Open
SI Sulfonimidates and Sulfonamides revision.pdfSupporting information6.51 MBAdobe PDFView/Open
Title: Highly chemoselective NH- and O-transfer to thiols using hypervalent iodine reagents: synthesis of sulfonimidates and sulfonamides
Authors: Tota, A
St John-Campbell, S
Briggs, E
Ogalla Estévez, G
Afonso, M
Degennaro, L
Luisi, R
Bull, JA
Item 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.
Issue Date: 13-Apr-2018
Date of Acceptance: 11-Apr-2018
URI: http://hdl.handle.net/10044/1/59016
DOI: https://dx.doi.org/10.1021/acs.orglett.8b00788
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/Funder: Engineering & Physical Science Research Council (EPSRC)
Engineering & Physical Science Research Council (E
The Royal Society
Funder's Grant Number: EP/J001538/1
EP/K503733/1
UF140161
Keywords: 03 Chemical Sciences
Organic Chemistry
Publication Status: Published
Appears in Collections:Chemistry
Faculty of Natural Sciences



Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

Creative Commons