These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
submitted on 04.01.2019, 21:13 and posted on 07.01.2019, 17:28by Patrick Fier, Kevin M. Maloney
Herein we describe the development and
application of a method for the mild, late-stage conversion of primary
sulfonamides to several other other functional groups. These reactions occur
via initial reductive deamination of sulfonamides to sulfinates via an
NHC-catalyzed reaction of transiently formed N-sulfonylimines. The method described here is tolerant of nearly
all common functional groups, as exemplified by the late-stage derivatization
of several complex pharmaceutical compounds. Based on the prevalence of
sulfonamide-containing drugs and building blocks, we have developed a method to
enable sulfonamides to be applied as versatile synthetic handles for synthetic