Thiocyanate promoted difunctionalization and cyclization of unsaturated C-C bonds to construct 1-sulfur-2-nitrogen-functionalized alkenes and 2-thiocyanate indolines
An unprecedented one-pot route to achieve highly regioselective 1-sulfur-functionalized 2-nitrogen-functionalized alkenes and 2-thiocyanate indolines from unsymmetrical ynamides (readily and generally available amides) using the commercially available inexpensive iodobenzene diacetate (PIDA) as the...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2024-02, Vol.22 (6), p.1213-1218 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Qin, Hong Chen, Feng Du, Jinze Yang, Xiaobing Huang, Yiping Zhu, Kai Yue, Changhai Fang, Zheng Guo, Kai |
| description | An unprecedented one-pot route to achieve highly regioselective 1-sulfur-functionalized 2-nitrogen-functionalized alkenes and 2-thiocyanate indolines from unsymmetrical ynamides (readily and generally available amides) using the commercially available inexpensive iodobenzene diacetate (PIDA) as the oxidant and potassium thiocyanate (KSCN) as the thiocyanate (SCN) source has been developed. The interconversion of thiocyanate (SCN) and isothiocyanate (NCS) groups simultaneously forms C-N and C-S bonds in this metal-free approach, while introducing important functional groups into homemade alkynes. A radical-chain mechanism, involving competing kinetically controlled chain transfer at the S atom and sterically-controlled chain transfer at the N atom of the thiocyanogen molecule in this mild approach, is proposed.
A facile approach to construct C-N and C-S bonds simultaneously and access various disubstituted alkenes and 2-thiocyanate indolines was developed. |
| doi_str_mv | 10.1039/d3ob01864d |
| format | Article |
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A facile approach to construct C-N and C-S bonds simultaneously and access various disubstituted alkenes and 2-thiocyanate indolines was developed.</description><subject>Alkenes</subject><subject>Alkynes</subject><subject>Amides</subject><subject>Chain transfer</subject><subject>Covalent bonds</subject><subject>Functional groups</subject><subject>Heterocyclic compounds</subject><subject>Nitrogen</subject><subject>Oxidants</subject><subject>Oxidizing agents</subject><subject>Potassium</subject><subject>Sulfur</subject><subject>Thiocyanates</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkUlPBCEQhYnRuF-8a0i8GBOUpZsejjrjlph40XOHBlrRHlCWw_h__J8yjo7GE0XeV6-gHgB7BJ8QzMSpZr7DZMQrvQI2SdU0CNdMrC5rijfAVozPGBPR8GodbLARpVzwZhN83D9Zr2bSyWTga_BTn4yG2vbZqWS9k4N9l_MCSqehmqnl3fcwuyhTDnLeMkZj2HmnI0weKu9iClklSFDMQ58DosjZFPyjceivd-mUw4txJn4NoCj9eY912g-2aDtgrZdDNLvf5zZ4uLy4H1-j27urm_HZLVJU8IQMI9Wo6xrZ4UpjwSgRkmJVY2P6EWWVqOuak7oITOkak44LphsicOnhFcZsGxwtfMsm3rKJqZ3aqMwwSGd8ji0VpDiImvKCHv5Dn30O5U9zitKyYNZUhTpeUCr4GIPp29dgpzLMWoLbeXjthN2df4U3KfDBt2XupkYv0Z-0CrC_AEJUS_U3ffYJk3Kgow</recordid><startdate>20240207</startdate><enddate>20240207</enddate><creator>Qin, Hong</creator><creator>Chen, Feng</creator><creator>Du, Jinze</creator><creator>Yang, Xiaobing</creator><creator>Huang, Yiping</creator><creator>Zhu, Kai</creator><creator>Yue, Changhai</creator><creator>Fang, Zheng</creator><creator>Guo, Kai</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3209-4713</orcidid><orcidid>https://orcid.org/0000-0002-0013-3263</orcidid></search><sort><creationdate>20240207</creationdate><title>Thiocyanate promoted difunctionalization and cyclization of unsaturated C-C bonds to construct 1-sulfur-2-nitrogen-functionalized alkenes and 2-thiocyanate indolines</title><author>Qin, Hong ; Chen, Feng ; Du, Jinze ; Yang, Xiaobing ; Huang, Yiping ; Zhu, Kai ; Yue, Changhai ; Fang, Zheng ; Guo, Kai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c296t-e3148bb7ab04d093219a20c50eef823495556159323cd501b693d7190bb764003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alkenes</topic><topic>Alkynes</topic><topic>Amides</topic><topic>Chain transfer</topic><topic>Covalent bonds</topic><topic>Functional groups</topic><topic>Heterocyclic compounds</topic><topic>Nitrogen</topic><topic>Oxidants</topic><topic>Oxidizing agents</topic><topic>Potassium</topic><topic>Sulfur</topic><topic>Thiocyanates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Qin, Hong</creatorcontrib><creatorcontrib>Chen, Feng</creatorcontrib><creatorcontrib>Du, Jinze</creatorcontrib><creatorcontrib>Yang, Xiaobing</creatorcontrib><creatorcontrib>Huang, Yiping</creatorcontrib><creatorcontrib>Zhu, Kai</creatorcontrib><creatorcontrib>Yue, Changhai</creatorcontrib><creatorcontrib>Fang, Zheng</creatorcontrib><creatorcontrib>Guo, Kai</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Qin, Hong</au><au>Chen, Feng</au><au>Du, Jinze</au><au>Yang, Xiaobing</au><au>Huang, Yiping</au><au>Zhu, Kai</au><au>Yue, Changhai</au><au>Fang, Zheng</au><au>Guo, Kai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thiocyanate promoted difunctionalization and cyclization of unsaturated C-C bonds to construct 1-sulfur-2-nitrogen-functionalized alkenes and 2-thiocyanate indolines</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2024-02-07</date><risdate>2024</risdate><volume>22</volume><issue>6</issue><spage>1213</spage><epage>1218</epage><pages>1213-1218</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>An unprecedented one-pot route to achieve highly regioselective 1-sulfur-functionalized 2-nitrogen-functionalized alkenes and 2-thiocyanate indolines from unsymmetrical ynamides (readily and generally available amides) using the commercially available inexpensive iodobenzene diacetate (PIDA) as the oxidant and potassium thiocyanate (KSCN) as the thiocyanate (SCN) source has been developed. The interconversion of thiocyanate (SCN) and isothiocyanate (NCS) groups simultaneously forms C-N and C-S bonds in this metal-free approach, while introducing important functional groups into homemade alkynes. A radical-chain mechanism, involving competing kinetically controlled chain transfer at the S atom and sterically-controlled chain transfer at the N atom of the thiocyanogen molecule in this mild approach, is proposed.
A facile approach to construct C-N and C-S bonds simultaneously and access various disubstituted alkenes and 2-thiocyanate indolines was developed.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38226967</pmid><doi>10.1039/d3ob01864d</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-3209-4713</orcidid><orcidid>https://orcid.org/0000-0002-0013-3263</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2024-02, Vol.22 (6), p.1213-1218 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alkenes Alkynes Amides Chain transfer Covalent bonds Functional groups Heterocyclic compounds Nitrogen Oxidants Oxidizing agents Potassium Sulfur Thiocyanates |
| title | Thiocyanate promoted difunctionalization and cyclization of unsaturated C-C bonds to construct 1-sulfur-2-nitrogen-functionalized alkenes and 2-thiocyanate indolines |
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