Formation of N-sulfonyl imines from iminoiodinanes by iodine-promoted, N-centered radical sulfonamidation of aldehydes

A mild and operationally convenient formation of synthetically valuable N-sulfonyl imines from a range of aryl aldehydes by reaction with iminoiodinanes (PhI[double bond, length as m-dash]NZ) and I has been developed. According to mechanistic experiments described within, the reaction is speculated...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017, Vol.15 (43), p.9209-9216
Main Authors: Hopkins, Megan D, Scott, Kristina A, DeMier, Brettany C, Morgan, Heather R, Macgruder, Jesse A, Lamar, Angus A
Format: Article
Language:English
Subjects:
Aldehydes
Aromatic compounds
Carbonyls
Imines
Iodine
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Summary:A mild and operationally convenient formation of synthetically valuable N-sulfonyl imines from a range of aryl aldehydes by reaction with iminoiodinanes (PhI[double bond, length as m-dash]NZ) and I has been developed. According to mechanistic experiments described within, the reaction is speculated to proceed through an unconventional light-promoted, N-centered radical (NCR) pathway involving a N,N-diiodosulfonamide reactive species. This method not only provides a new pathway toward the production of activated imines, but also serves as an example of a non-traditional means of carbonyl activation via an NCR species.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob02120h