Formation of N-sulfonyl imines from iminoiodinanes by iodine-promoted, N-centered radical sulfonamidation of aldehydes. Issue 43 (27th October 2017)

• Record Type: Journal Article
• Authors: Hopkins, Megan D.; Scott, Kristina A.; DeMier, Brettany C.; Morgan, Heather R.; Macgruder, Jesse A.; Lamar, Angus A.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 43(2017)
• Page Start: 9209
• Page End: 9216
• Publication Date: 2017-10-27
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob02120h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A light-promoted, non-traditional carbonyl activation via a N-centered radical (NCR) species to produce activated imines using iminoiodinanes is reported. Abstract : A mild and operationally convenient formation of synthetically valuable N -sulfonyl imines from a range of aryl aldehydes by reaction with iminoiodinanes (PhINZ) and I2 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.