Access to 5- to 14-Membered <i>N</i>‑Heterocyclesby Alkylamination of 1,3-Dienes via Palladium Catalysis

Medium-sized rings show great potential in medicinal chemistry but are difficult to achieve via direct cyclization reaction. We herein report a versatile and mild photocatalytic approach for synthesis of medium- and large-sized vinyl <i>N</i>-heterocycles by radical-mediated cyclization of sulfonamides with pendant 1,3-dienes. The reaction involves the generation of radicals from alkyl halides and cyclization of π-allylpalladium species. This method could serve as a versatile platform for the construction of <i>N</i>-heterocycles with medium- and large-sized rings via Pd catalysis.

Publication Details

Journal
Figshare
Published
2025-03-13
DOI
https://doi.org/10.1021/acs.orglett.5c00508.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
Field-Weighted Citation Impact
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article

Access to 5- to 14-Membered N‑Heterocyclesby Alkylamination of 1,3-Dienes via Palladium Catalysis

Figshare
Mycorrhizal Fungi and Plant Interactions
article

Access to 5- to 14-Membered N‑Heterocyclesby Alkylamination of 1,3-Dienes via Palladium Catalysis

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Abstract

Medium-sized rings show great potential in medicinal chemistry but are difficult to achieve via direct cyclization reaction. We herein report a versatile and mild photocatalytic approach for synthesis of medium- and large-sized vinyl <i>N</i>-heterocycles by radical-mediated cyclization of sulfonamides with pendant 1,3-dienes. The reaction involves the generation of radicals from alkyl halides and cyclization of π-allylpalladium species. This method could serve as a versatile platform for the construction of <i>N</i>-heterocycles with medium- and large-sized rings via Pd catalysis.

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Mycorrhizal Fungi and Plant Interactions
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Access to 5- to 14-Membered <i>N</i>‑Heterocyclesby Alkylamination of 1,3-Dienes via Palladium Catalysis · Figshare (2025) | TGRS Research Map | TGRS