KF and Diaryl Iodide Salt-Mediated Ring Opening of Silacyclobutanes with Carbon Disulfide and Amines to Generate 3-(Fluorosilyl)propyl Dithiocarbamates

An unprecedented strategy for the ring-opening transformation of silacyclobutanes using potassium fluoride and diaryliodonium salts has been developed. In this multicomponent reaction, silacyclobutanes undergo ring opening mediated by potassium fluoride and diaryliodonium salts, followed by reaction with in situ-generated dithioaminoacetic acid to afford 3-(fluorosilyl)propyl dithiocarbamates. This study has expanded the potential applications of the silicon-containing building block silacyclobutanes, successfully achieving their silicon-carbon dual functionalization under metal catalyst-free conditions.

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Publication Details

Journal
Organic Letters
Published
2025-12-11
DOI
https://doi.org/10.1021/acs.orglett.5c04593
Primary Topic
Organoboron and organosilicon chemistry
Type
article
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article

KF and Diaryl Iodide Salt-Mediated Ring Opening of Silacyclobutanes with Carbon Disulfide and Amines to Generate 3-(Fluorosilyl)propyl Dithiocarbamates

Xiao‐Ming Ren, Zhenchen Tang, Rulong Yan, Peihua Liu et al.
Organic Letters
Organoboron and organosilicon chemistry
article

KF and Diaryl Iodide Salt-Mediated Ring Opening of Silacyclobutanes with Carbon Disulfide and Amines to Generate 3-(Fluorosilyl)propyl Dithiocarbamates

Xiao‐Ming Ren, Zhenchen Tang, Rulong Yan, Peihua Liu, Shuairan Wang, Jiaze Qin, Mingyu Guan
article en

Abstract

An unprecedented strategy for the ring-opening transformation of silacyclobutanes using potassium fluoride and diaryliodonium salts has been developed. In this multicomponent reaction, silacyclobutanes undergo ring opening mediated by potassium fluoride and diaryliodonium salts, followed by reaction with in situ-generated dithioaminoacetic acid to afford 3-(fluorosilyl)propyl dithiocarbamates. This study has expanded the potential applications of the silicon-containing building block silacyclobutanes, successfully achieving their silicon-carbon dual functionalization under metal catalyst-free conditions.

Organic LettersVol. 27(51)
Jinchuan (China) (CN), State Key Laboratory of Chemical Engineering (CN), Lanzhou University (CN)
Openalex Percentile: Top 70%
Organoboron and organosilicon chemistry
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