Electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes
An electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides with 2-bromoethan-1-ol as the brominating reagent has been developed. The paired electrolysis employs low concentrations of bromine produced from both cathodic reduction and anodic oxidation as an electrophile, an...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2023-05, Vol.25 (9), p.3543-3548 |
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| container_issue | 9 |
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| container_title | Green chemistry : an international journal and green chemistry resource : GC |
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| creator | Zhang, Zhongyi Hou, Zhong-Wei Chen, Hao Li, Pinhua Wang, Lei |
| description | An electrochemical electrophilic bromination/spirocyclization of
N
-benzyl-acrylamides with 2-bromoethan-1-ol as the brominating reagent has been developed. The paired electrolysis employs low concentrations of bromine produced from both cathodic reduction and anodic oxidation as an electrophile, and realizes an H
2
O-involved electrophilic spirocyclization. A number of unexplored brominated 2-azaspiro[4.5]decanes are obtained with satisfactory yields under mild conditions, and the reaction exhibits good efficiency at the gram-scale synthesis. In addition, this approach is further highlighted by late-stage transformations and synthetic applications in constructing cyclohepta[
c
]pyrrole-1,6-diones
via
debromination tandem cyclization of brominated 2-azaspiro[4.5]decanes. |
| doi_str_mv | 10.1039/D3GC00728F |
| format | Article |
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N
-benzyl-acrylamides with 2-bromoethan-1-ol as the brominating reagent has been developed. The paired electrolysis employs low concentrations of bromine produced from both cathodic reduction and anodic oxidation as an electrophile, and realizes an H
2
O-involved electrophilic spirocyclization. A number of unexplored brominated 2-azaspiro[4.5]decanes are obtained with satisfactory yields under mild conditions, and the reaction exhibits good efficiency at the gram-scale synthesis. In addition, this approach is further highlighted by late-stage transformations and synthetic applications in constructing cyclohepta[
c
]pyrrole-1,6-diones
via
debromination tandem cyclization of brominated 2-azaspiro[4.5]decanes.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/D3GC00728F</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Anodizing ; Bromination ; Bromine ; Chemical reduction ; Electrochemistry ; Electrolysis ; Green chemistry ; Low concentrations ; Oxidation ; Reagents</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2023-05, Vol.25 (9), p.3543-3548</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c300t-5e96a192cd43e6dbf3cd40c6a29f287016f38a96f4d4c032d95056ae24d793933</citedby><cites>FETCH-LOGICAL-c300t-5e96a192cd43e6dbf3cd40c6a29f287016f38a96f4d4c032d95056ae24d793933</cites><orcidid>0000-0001-6580-7671 ; 0000-0002-8528-8087</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Zhang, Zhongyi</creatorcontrib><creatorcontrib>Hou, Zhong-Wei</creatorcontrib><creatorcontrib>Chen, Hao</creatorcontrib><creatorcontrib>Li, Pinhua</creatorcontrib><creatorcontrib>Wang, Lei</creatorcontrib><title>Electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>An electrochemical electrophilic bromination/spirocyclization of
N
-benzyl-acrylamides with 2-bromoethan-1-ol as the brominating reagent has been developed. The paired electrolysis employs low concentrations of bromine produced from both cathodic reduction and anodic oxidation as an electrophile, and realizes an H
2
O-involved electrophilic spirocyclization. A number of unexplored brominated 2-azaspiro[4.5]decanes are obtained with satisfactory yields under mild conditions, and the reaction exhibits good efficiency at the gram-scale synthesis. In addition, this approach is further highlighted by late-stage transformations and synthetic applications in constructing cyclohepta[
c
]pyrrole-1,6-diones
via
debromination tandem cyclization of brominated 2-azaspiro[4.5]decanes.</description><subject>Anodizing</subject><subject>Bromination</subject><subject>Bromine</subject><subject>Chemical reduction</subject><subject>Electrochemistry</subject><subject>Electrolysis</subject><subject>Green chemistry</subject><subject>Low concentrations</subject><subject>Oxidation</subject><subject>Reagents</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpFkF9LwzAUxYMoOKcvfoKAb0K2_GvaPMrcpjD0RZ9ESpakLCNtatKB3ae3bjKf7rmX37kHDgC3BE8IZnL6yJYzjHNaLM7AiHDBkKQ5Pj9pQS_BVUpbjAnJBR-B77m3uotBb2zttPLQHvd247zTcB1D7RrVudBMU-sGrtfe7Q8HGCr4AtHaNvveI6Vj71XtjE2wCyejNZAitVcH8wefZJ_GatXYdA0uKuWTvfmbY_C-mL_NntDqdfk8e1ghzTDuUGalUERSbTizwqwrNiishaKyokWOiahYoaSouOEaM2pkhjOhLOUml0wyNgZ3x79tDF87m7pyG3axGSJLWpChBUopH6j7I6VjSCnaqmyjq1XsS4LL32bL_2bZD0McbNg</recordid><startdate>20230509</startdate><enddate>20230509</enddate><creator>Zhang, Zhongyi</creator><creator>Hou, Zhong-Wei</creator><creator>Chen, Hao</creator><creator>Li, Pinhua</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><orcidid>https://orcid.org/0000-0002-8528-8087</orcidid></search><sort><creationdate>20230509</creationdate><title>Electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes</title><author>Zhang, Zhongyi ; Hou, Zhong-Wei ; Chen, Hao ; Li, Pinhua ; Wang, Lei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c300t-5e96a192cd43e6dbf3cd40c6a29f287016f38a96f4d4c032d95056ae24d793933</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Anodizing</topic><topic>Bromination</topic><topic>Bromine</topic><topic>Chemical reduction</topic><topic>Electrochemistry</topic><topic>Electrolysis</topic><topic>Green chemistry</topic><topic>Low concentrations</topic><topic>Oxidation</topic><topic>Reagents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Zhongyi</creatorcontrib><creatorcontrib>Hou, Zhong-Wei</creatorcontrib><creatorcontrib>Chen, Hao</creatorcontrib><creatorcontrib>Li, Pinhua</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>Zhang, Zhongyi</au><au>Hou, Zhong-Wei</au><au>Chen, Hao</au><au>Li, Pinhua</au><au>Wang, Lei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2023-05-09</date><risdate>2023</risdate><volume>25</volume><issue>9</issue><spage>3543</spage><epage>3548</epage><pages>3543-3548</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>An electrochemical electrophilic bromination/spirocyclization of
N
-benzyl-acrylamides with 2-bromoethan-1-ol as the brominating reagent has been developed. The paired electrolysis employs low concentrations of bromine produced from both cathodic reduction and anodic oxidation as an electrophile, and realizes an H
2
O-involved electrophilic spirocyclization. A number of unexplored brominated 2-azaspiro[4.5]decanes are obtained with satisfactory yields under mild conditions, and the reaction exhibits good efficiency at the gram-scale synthesis. In addition, this approach is further highlighted by late-stage transformations and synthetic applications in constructing cyclohepta[
c
]pyrrole-1,6-diones
via
debromination tandem cyclization of brominated 2-azaspiro[4.5]decanes.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D3GC00728F</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-6580-7671</orcidid><orcidid>https://orcid.org/0000-0002-8528-8087</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2023-05, Vol.25 (9), p.3543-3548 |
| issn | 1463-9262 1463-9270 |
| language | eng |
| recordid | cdi_proquest_journals_2811172224 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Anodizing Bromination Bromine Chemical reduction Electrochemistry Electrolysis Green chemistry Low concentrations Oxidation Reagents |
| title | Electrochemical electrophilic bromination/spirocyclization of N -benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes |
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