Sulfilimine benziodoxolones: stable electrophilic bifunctional reagents for nitrogen incorporation
Abstract
We report the design and scalable synthesis of novel sulfilimine-based hypervalent iodine reagents (INSert, based on the I-N=S motif), that are bench-stable, non-explosive and can act as bifunctional electrophilic nitrogen donors. Their distinctive architecture combines a benziodoxolone moiety to induce electrophilicity at the nitrogen atom, with a sulfilimine group as a versatile, latent synthetic handle for downstream diversification. We first demonstrate the utility of this reagent class through the formal anti-Markovnikov hydrosulfilimination of alkenes via alkyldimethylborane intermediates, followed by subsequent transformation of the resulting N-alkylsulfilimine into various nitrogen-containing scaffolds. We also report preliminary N-insertion reactions with an indole and an imidazole. These results clearly show that the reagents’ modular iodinane-sulfilimine architecture can open new avenues for the incorporation of nitrogen into organic molecules through multiple distinct reaction manifolds.
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BibTeX
@misc{suponytskyi2026sulfilimine,
title = {{Sulfilimine benziodoxolones: stable electrophilic bifunctional reagents for nitrogen incorporation}},
author = {Andrii Suponytskyi and Patrick W. Fritz and Mykola Avramenko and Lucia Invernizzi and Gian Carmine Conigliaro and Lara Kirchberg and Leonard Kreft and Bill Morandi},
howpublished = {ChemRxiv},
year = {2026},
month = oct,
doi = {10.26434/chemrxiv.15009957/v1},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009957/v1},
note = {CC BY},
}
RIS
TY - UNPB
TI - Sulfilimine benziodoxolones: stable electrophilic bifunctional reagents for nitrogen incorporation
AU - Andrii Suponytskyi
AU - Patrick W. Fritz
AU - Mykola Avramenko
AU - Lucia Invernizzi
AU - Gian Carmine Conigliaro
AU - Lara Kirchberg
AU - Leonard Kreft
AU - Bill Morandi
PY - 2026
DA - 2026/10/05
PB - ChemRxiv
DO - 10.26434/chemrxiv.15009957/v1
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009957/v1
AB - We report the design and scalable synthesis of novel sulfilimine-based hypervalent iodine reagents (INSert, based on the I-N=S motif), that are bench-stable, non-explosive and can act as bifunctional electrophilic nitrogen donors. Their distinctive architecture combines a benziodoxolone moiety to induce electrophilicity at the nitrogen atom, with a sulfilimine group as a versatile, latent synthetic handle for downstream diversification. We first demonstrate the utility of this reagent class through the formal anti-Markovnikov hydrosulfilimination of alkenes via alkyldimethylborane intermediates, followed by subsequent transformation of the resulting N-alkylsulfilimine into various nitrogen-containing scaffolds. We also report preliminary N-insertion reactions with an indole and an imidazole. These results clearly show that the reagents’ modular iodinane-sulfilimine architecture can open new avenues for the incorporation of nitrogen into organic molecules through multiple distinct reaction manifolds.
ER -