Multistep Continuous Flow Synthesis of Isolable NH₂ -Sulfinamidines via Nucleophilic Addition to Transient Sulfurdiimide.

ABSTRACT: The growing interest in novel sulfur pharmacophores led to recent advances in the synthesis of some S(IV) and S(VI) motifs. However, preparation and isolation of uncommon primary sulfinamidines, the aza-analogues of sulfinamides, is highly desirable. Here we report a multistep continuous flow synthesis of poorly explored NH₂ -sulfinamidines by nucleophilic attack of organometallic reagents to in situ prepared N-(trimethylsilyl)-N-trityl-λ⁴ -sulfanediimine (Tr-N=S=N-TMS). The transformation can additionally be realized under mild conditions, at room temperature, via a highly chemoselective halogen-lithium exchange of aryl bromides and iodides with n-butyllithium. Moreover, the synthetic potential of the methodology was assessed by exploring further manipulations of the

SUBMITTER: Andresini M 

PROVIDER: S-EPMC9804385 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature