Electrooxidative tandem cyclization of N -propargylanilines with sulfinic acids for rapid access to 3-arylsulfonylquinoline derivatives
A series of N -propargylanilines (0.2 mmol) and sulfinic acids (0.5 mmol) afforded 3-arylsulfonylquinoline derivatives in high yields (70–93%) and low current efficiencies upon electrooxidation. Electrolyses were carried out in a one-compartment cell, under constant current and ambient conditions, i...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2021-07, Vol.23 (13), p.4733-4740 |
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| container_title | Green chemistry : an international journal and green chemistry resource : GC |
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| creator | Liu, Jie Wang, Min Li, Laiqiang Wang, Lei |
| description | A series of
N
-propargylanilines (0.2 mmol) and sulfinic acids (0.5 mmol) afforded 3-arylsulfonylquinoline derivatives in high yields (70–93%) and low current efficiencies upon electrooxidation. Electrolyses were carried out in a one-compartment cell, under constant current and ambient conditions, in methanol-
n
Bu
4
NBF
4
containing pyridine (0.4 mmol), without any added chemical oxidant. A scale-up electrolysis carried out on 5 mmol of
N
-propargylaniline
1a
gave 3-arylsulfonylquinoline
3aa
in 65% yield and 56% current efficiency. A mechanistic hypothesis is presented. |
| doi_str_mv | 10.1039/D1GC00171J |
| format | Article |
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N
-propargylanilines (0.2 mmol) and sulfinic acids (0.5 mmol) afforded 3-arylsulfonylquinoline derivatives in high yields (70–93%) and low current efficiencies upon electrooxidation. Electrolyses were carried out in a one-compartment cell, under constant current and ambient conditions, in methanol-
n
Bu
4
NBF
4
containing pyridine (0.4 mmol), without any added chemical oxidant. A scale-up electrolysis carried out on 5 mmol of
N
-propargylaniline
1a
gave 3-arylsulfonylquinoline
3aa
in 65% yield and 56% current efficiency. A mechanistic hypothesis is presented.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/D1GC00171J</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Acids ; Current efficiency ; Electrolysis ; Green chemistry ; Low currents ; Oxidants ; Oxidizing agents ; Pyridines ; Scale (corrosion)</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2021-07, Vol.23 (13), p.4733-4740</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c189t-e062fcd9b5e7662ea1135653a7822aee74ce60656838aeb88d4b5c64c00c53953</citedby><cites>FETCH-LOGICAL-c189t-e062fcd9b5e7662ea1135653a7822aee74ce60656838aeb88d4b5c64c00c53953</cites><orcidid>0000-0001-6580-7671</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Liu, Jie</creatorcontrib><creatorcontrib>Wang, Min</creatorcontrib><creatorcontrib>Li, Laiqiang</creatorcontrib><creatorcontrib>Wang, Lei</creatorcontrib><title>Electrooxidative tandem cyclization of N -propargylanilines with sulfinic acids for rapid access to 3-arylsulfonylquinoline derivatives</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>A series of
N
-propargylanilines (0.2 mmol) and sulfinic acids (0.5 mmol) afforded 3-arylsulfonylquinoline derivatives in high yields (70–93%) and low current efficiencies upon electrooxidation. Electrolyses were carried out in a one-compartment cell, under constant current and ambient conditions, in methanol-
n
Bu
4
NBF
4
containing pyridine (0.4 mmol), without any added chemical oxidant. A scale-up electrolysis carried out on 5 mmol of
N
-propargylaniline
1a
gave 3-arylsulfonylquinoline
3aa
in 65% yield and 56% current efficiency. A mechanistic hypothesis is presented.</description><subject>Acids</subject><subject>Current efficiency</subject><subject>Electrolysis</subject><subject>Green chemistry</subject><subject>Low currents</subject><subject>Oxidants</subject><subject>Oxidizing agents</subject><subject>Pyridines</subject><subject>Scale (corrosion)</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpFkMtOwzAURC0EEqWw4QsssUMK-BE7yRKVtoAq2MA6cp0bcOXaqZ0Uwg_w26QUweo-dDSjGYTOKbmihBfXt3Q-IYRm9OEAjWgqeVKwjBz-7ZIdo5MYVwNDM5mO0NfUgm6D9x-mUq3ZAm6Vq2CNda-t-Rxe3mFf40ecNME3Krz2VjljjYOI3037hmNna-OMxkqbKuLaBxxUY6rh1hAjbj3miQq93YHe9XbTGed3AriCYLY_rvEUHdXKRjj7nWP0Mps-T-6SxdP8fnKzSDTNizYBIlmtq2IpIJOSgaKUCym4ynLGFECWapBECpnzXMEyz6t0KbRMNSFa8ELwMbrY6w5pNh3Etlz5LrjBsmQizXlKpWADdbmndPAxBqjLJpj1EKKkpNwVXf4Xzb8BMCZzIw</recordid><startdate>20210707</startdate><enddate>20210707</enddate><creator>Liu, Jie</creator><creator>Wang, Min</creator><creator>Li, Laiqiang</creator><creator>Wang, Lei</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U6</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0001-6580-7671</orcidid></search><sort><creationdate>20210707</creationdate><title>Electrooxidative tandem cyclization of N -propargylanilines with sulfinic acids for rapid access to 3-arylsulfonylquinoline derivatives</title><author>Liu, Jie ; Wang, Min ; Li, Laiqiang ; Wang, Lei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c189t-e062fcd9b5e7662ea1135653a7822aee74ce60656838aeb88d4b5c64c00c53953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Acids</topic><topic>Current efficiency</topic><topic>Electrolysis</topic><topic>Green chemistry</topic><topic>Low currents</topic><topic>Oxidants</topic><topic>Oxidizing agents</topic><topic>Pyridines</topic><topic>Scale (corrosion)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Jie</creatorcontrib><creatorcontrib>Wang, Min</creatorcontrib><creatorcontrib>Li, Laiqiang</creatorcontrib><creatorcontrib>Wang, Lei</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Materials Research Database</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Jie</au><au>Wang, Min</au><au>Li, Laiqiang</au><au>Wang, Lei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrooxidative tandem cyclization of N -propargylanilines with sulfinic acids for rapid access to 3-arylsulfonylquinoline derivatives</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2021-07-07</date><risdate>2021</risdate><volume>23</volume><issue>13</issue><spage>4733</spage><epage>4740</epage><pages>4733-4740</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>A series of
N
-propargylanilines (0.2 mmol) and sulfinic acids (0.5 mmol) afforded 3-arylsulfonylquinoline derivatives in high yields (70–93%) and low current efficiencies upon electrooxidation. Electrolyses were carried out in a one-compartment cell, under constant current and ambient conditions, in methanol-
n
Bu
4
NBF
4
containing pyridine (0.4 mmol), without any added chemical oxidant. A scale-up electrolysis carried out on 5 mmol of
N
-propargylaniline
1a
gave 3-arylsulfonylquinoline
3aa
in 65% yield and 56% current efficiency. A mechanistic hypothesis is presented.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D1GC00171J</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-6580-7671</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2021-07, Vol.23 (13), p.4733-4740 |
| issn | 1463-9262 1463-9270 |
| language | eng |
| recordid | cdi_proquest_journals_2548341652 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Acids Current efficiency Electrolysis Green chemistry Low currents Oxidants Oxidizing agents Pyridines Scale (corrosion) |
| title | Electrooxidative tandem cyclization of N -propargylanilines with sulfinic acids for rapid access to 3-arylsulfonylquinoline derivatives |
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