Cargando…
Mild, Efficient, and Metal-Free Radical 1,2-Dithiocyanation of Alkynes and Alkenes at Room Temperature
[Image: see text] 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 con...
Autores principales: | , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2018
|
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644369/ https://www.ncbi.nlm.nih.gov/pubmed/31458029 http://dx.doi.org/10.1021/acsomega.8b01762 |
_version_ | 1783437239050567680 |
---|---|
author | Samanta, Satyajit Chatterjee, Rana Santra, Sougata Hajra, Alakananda Khalymbadzha, Igor A. Zyryanov, Grigory V. Majee, Adinath |
author_facet | Samanta, Satyajit Chatterjee, Rana Santra, Sougata Hajra, Alakananda Khalymbadzha, Igor A. Zyryanov, Grigory V. Majee, Adinath |
author_sort | Samanta, Satyajit |
collection | PubMed |
description | [Image: see text] 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. |
format | Online Article Text |
id | pubmed-6644369 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-66443692019-08-27 Mild, Efficient, and Metal-Free Radical 1,2-Dithiocyanation of Alkynes and Alkenes at Room Temperature Samanta, Satyajit Chatterjee, Rana Santra, Sougata Hajra, Alakananda Khalymbadzha, Igor A. Zyryanov, Grigory V. Majee, Adinath ACS Omega [Image: see text] 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. American Chemical Society 2018-10-11 /pmc/articles/PMC6644369/ /pubmed/31458029 http://dx.doi.org/10.1021/acsomega.8b01762 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Samanta, Satyajit Chatterjee, Rana Santra, Sougata Hajra, Alakananda Khalymbadzha, Igor A. Zyryanov, Grigory V. Majee, Adinath Mild, Efficient, and Metal-Free Radical 1,2-Dithiocyanation of Alkynes and Alkenes at Room Temperature |
title | Mild, Efficient, and Metal-Free Radical 1,2-Dithiocyanation
of Alkynes and Alkenes at Room Temperature |
title_full | Mild, Efficient, and Metal-Free Radical 1,2-Dithiocyanation
of Alkynes and Alkenes at Room Temperature |
title_fullStr | Mild, Efficient, and Metal-Free Radical 1,2-Dithiocyanation
of Alkynes and Alkenes at Room Temperature |
title_full_unstemmed | Mild, Efficient, and Metal-Free Radical 1,2-Dithiocyanation
of Alkynes and Alkenes at Room Temperature |
title_short | Mild, Efficient, and Metal-Free Radical 1,2-Dithiocyanation
of Alkynes and Alkenes at Room Temperature |
title_sort | mild, efficient, and metal-free radical 1,2-dithiocyanation
of alkynes and alkenes at room temperature |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644369/ https://www.ncbi.nlm.nih.gov/pubmed/31458029 http://dx.doi.org/10.1021/acsomega.8b01762 |
work_keys_str_mv | AT samantasatyajit mildefficientandmetalfreeradical12dithiocyanationofalkynesandalkenesatroomtemperature AT chatterjeerana mildefficientandmetalfreeradical12dithiocyanationofalkynesandalkenesatroomtemperature AT santrasougata mildefficientandmetalfreeradical12dithiocyanationofalkynesandalkenesatroomtemperature AT hajraalakananda mildefficientandmetalfreeradical12dithiocyanationofalkynesandalkenesatroomtemperature AT khalymbadzhaigora mildefficientandmetalfreeradical12dithiocyanationofalkynesandalkenesatroomtemperature AT zyryanovgrigoryv mildefficientandmetalfreeradical12dithiocyanationofalkynesandalkenesatroomtemperature AT majeeadinath mildefficientandmetalfreeradical12dithiocyanationofalkynesandalkenesatroomtemperature |