Abstract
Diarylation of N- and O-nucleophiles through a metal-free cascade reaction
Highlights
N- and O-arylated structural motifs are key building blocks in agrochemicals, materials, and pharmaceuticals.[1,2,3] The arylation of heteroatom nucleophiles with an electrophilic arylation reagent is a central strategy to reach diarylated compound classes, such as diaryl ethers and diarylamines
Monoarylation of heteroatom nucleophiles can be achieved through the industrially important nucleophilic aromatic substitution (SNAr) methodology, the scope is limited by the requirement for either highly reactive reagents with strong electron-withdrawing groups (EWG) or harsh reaction conditions with strong bases or elevated temperatures (Scheme 1A).[4]
We present the realization of this strategy, which enables a metal-free, high-yielding difunctionalization of N- and O-nucleophiles with two different aryl groups in a single reaction (Scheme 1D)
Summary
N- and O-arylated structural motifs are key building blocks in agrochemicals, materials, and pharmaceuticals.[1,2,3] The arylation of heteroatom nucleophiles with an electrophilic arylation reagent is a central strategy to reach diarylated compound classes, such as diaryl ethers and diarylamines. We speculated that the unusual structure of this reagent might enable an initial SNAr reaction instead of the usual ligand coupling (LC) pathway[11,35] to deliver a unique iodine(III) intermediate that could undergo a subsequent aryl transfer to yield a diarylated product.
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
