Fluorosulfuryl Isocyanate Enabled SuFEx Ligation of Alcohols and Amines.

ABSTRACT: Fluorosulfuryl isocyanate (FSI, FSO₂ NCO) is established as a reliable bis-electrophilic linker for stepwise attachment of an alcohol bearing module to an amine bearing module and thence a new module RO-C(=O)-NH-SO₂ -NR'R'' is created. FSI's isocyanate motif fuses directly and quickly with alcohols and phenols, affording fluorosulfuryl carbamates in nearly quantitative yield. A new reagent and process to deliver the FSI-derived fluorosulfuryl carbamate fragment to amines are also developed. The resulting S^VI -F motifs from step-1 are remarkably stable, given the great structural complexities in diverse products. In the step-2 reaction with amines, the best yield of the S-N linked products arise with water alone. This "on water" interfacial reactivity phenom

SUBMITTER: Sun S 

PROVIDER: S-EPMC9881234 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature