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温和、高效且无金属催化的炔烃和烯烃在室温下的自由基1,2-二硫氰化反应

Mild, Efficient, and Metal-Free Radical 1,2-Dithiocyanation of Alkynes and Alkenes at Room Temperature.

作者信息

Samanta Satyajit, Chatterjee Rana, Santra Sougata, Hajra Alakananda, Khalymbadzha Igor A, Zyryanov Grigory V, Majee Adinath

机构信息

Department of Chemistry, Visva-Bharati (A Central University), Santiniketan 731235, India.

Department of Organic & Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, 19 Mira Str., Yekaterinburg 620002, Russian Federation.

出版信息

ACS Omega. 2018 Oct 11;3(10):13081-13088. doi: 10.1021/acsomega.8b01762. eCollection 2018 Oct 31.

DOI:10.1021/acsomega.8b01762
PMID:31458029
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6644369/
Abstract

A transition metal-free process has been reported for 1,2-dithiocyanation of alkynes in the presence of sodium persulfate and potassium thiocyanate reagent combination in a short reaction time under ambient air. Styrene derivatives are equally applicable under the same reaction conditions. Monothiocyanated vinyl derivatives were also synthesized from 2-ethynylpyridine and dimethyl acetylene dicarboxylate. The reaction proceeds by the radical/polar pathway as evidenced from our experiments and literature. After removal of the solvent from the reaction mixture by evaporation, the crude product was purified without conventional workup.

摘要

据报道,在过硫酸钠和硫氰酸钾试剂组合存在下,于环境空气中短反应时间内,可实现炔烃的无过渡金属1,2-二硫氰化反应。在相同反应条件下,苯乙烯衍生物同样适用。单硫氰化乙烯基衍生物也可由2-乙炔基吡啶和二甲基乙炔二羧酸酯合成。从我们的实验和文献可知,该反应通过自由基/极性途径进行。通过蒸发从反应混合物中除去溶剂后,粗产物无需常规后处理即可纯化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eefd/6644369/b3e66f24e63f/ao-2018-01762f_0009.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eefd/6644369/b3e66f24e63f/ao-2018-01762f_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eefd/6644369/c2294fe92725/ao-2018-01762f_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eefd/6644369/81e1dfd1a9f2/ao-2018-01762f_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eefd/6644369/dd3be1170d88/ao-2018-01762f_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eefd/6644369/6bf024547dca/ao-2018-01762f_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eefd/6644369/5cf9d6c1ecdc/ao-2018-01762f_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eefd/6644369/ec73149fb6dc/ao-2018-01762f_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eefd/6644369/1c00631e4bf0/ao-2018-01762f_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eefd/6644369/a9f786331c01/ao-2018-01762f_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eefd/6644369/b3e66f24e63f/ao-2018-01762f_0009.jpg

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