Iron-Promoted Sulfinative Cyclization of <i>N</i> -Bromoacetyl Cyanamide with Inorganic Sulfur Dioxide Surrogate via Radical-Polar Crossover Reaction

An iron-promoted sulfinative cyclization for the preparation of amidine-imbedded sultines under the mild conditions was described, in which available <i>N</i>-bromoacetyl cyanamide and easy-to-handle sodium dithionite, acting as an easy-to-handle sulfur dioxide surrogate and a readily reductant, facilitated the assembly of the target sultines via a radical-polar crossover pathway in a sustainable manner. This protocol is highly amenable to exploring the chemical space relevant to the construction of sulfur heterocycles incorporating nitrogen functionalities.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-18
DOI
https://doi.org/10.1021/acs.joc.5c02892
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Iron-Promoted Sulfinative Cyclization of N -Bromoacetyl Cyanamide with Inorganic Sulfur Dioxide Surrogate via Radical-Polar Crossover Reaction

Zhonglin Wei, Wei‐Wei Liao, Li Zheng, Yu-Jie Geng
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

Iron-Promoted Sulfinative Cyclization of N -Bromoacetyl Cyanamide with Inorganic Sulfur Dioxide Surrogate via Radical-Polar Crossover Reaction

Zhonglin Wei, Wei‐Wei Liao, Li Zheng, Yu-Jie Geng
article en

Abstract

An iron-promoted sulfinative cyclization for the preparation of amidine-imbedded sultines under the mild conditions was described, in which available <i>N</i>-bromoacetyl cyanamide and easy-to-handle sodium dithionite, acting as an easy-to-handle sulfur dioxide surrogate and a readily reductant, facilitated the assembly of the target sultines via a radical-polar crossover pathway in a sustainable manner. This protocol is highly amenable to exploring the chemical space relevant to the construction of sulfur heterocycles incorporating nitrogen functionalities.

The Journal of Organic ChemistryVol. 91(1)
Jilin University (CN), Chinese Academy of Sciences (CN), Shanghai Institute of Organic Chemistry (CN), State Key Laboratory of Organometallic Chemistry
Openalex Percentile: Top 69%
Sulfur-Based Synthesis Techniques
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Iron-Promoted Sulfinative Cyclization of <i>N</i> -Bromoacetyl Cyanamide with Inorganic Sulfur Dioxide Surrogate via Radical-Polar Crossover Reaction — Zhonglin Wei, Wei‐Wei Liao, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS