Visible-light-induced tandem difluoroalkylated spirocyclization of N -arylpropiolamides: access to C3-difluoroacetylated spiro[4,5]trienones
A visible-light-catalyzed difluoroacetylated spirocyclization of N -arylpropiolamides with ethyl bromodifluoroacetate as a CF 2 CO 2 Et radical precursor is described. This approach allows the formation of two carbon–carbon bonds and one carbon–oxygen bond in a single reaction through a sequence of...
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| Veröffentlicht in: | New journal of chemistry 2022-02, Vol.46 (9), p.4470-4482 |
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| container_end_page | 4482 |
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| container_issue | 9 |
| container_start_page | 4470 |
| container_title | New journal of chemistry |
| container_volume | 46 |
| creator | Yuan, Jin-Wei Shen, Lu Ma, Meng-Yao Feng, Shi Yang, Wan Yang, Liang-Ru Xiao, Yong-Mei Zhang, Shou-Ren Qu, Ling-Bo |
| description | A visible-light-catalyzed difluoroacetylated spirocyclization of
N
-arylpropiolamides with ethyl bromodifluoroacetate as a CF
2
CO
2
Et radical precursor is described. This approach allows the formation of two carbon–carbon bonds and one carbon–oxygen bond in a single reaction through a sequence of C–H oxidative coupling,
ipso
-cyclization and dearomatization processes. This protocol affords a straightforward route to synthesize CF
2
CO
2
Et-containing spiro[4.5]trienones in moderate to good yields. |
| doi_str_mv | 10.1039/D2NJ00131D |
| format | Article |
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N
-arylpropiolamides with ethyl bromodifluoroacetate as a CF
2
CO
2
Et radical precursor is described. This approach allows the formation of two carbon–carbon bonds and one carbon–oxygen bond in a single reaction through a sequence of C–H oxidative coupling,
ipso
-cyclization and dearomatization processes. This protocol affords a straightforward route to synthesize CF
2
CO
2
Et-containing spiro[4.5]trienones in moderate to good yields.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/D2NJ00131D</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Carbon ; Covalent bonds</subject><ispartof>New journal of chemistry, 2022-02, Vol.46 (9), p.4470-4482</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-a9eac9a964b85fa2becda07f41ec535c974904402618b97f3b8c3bcae1e0fc5f3</citedby><cites>FETCH-LOGICAL-c259t-a9eac9a964b85fa2becda07f41ec535c974904402618b97f3b8c3bcae1e0fc5f3</cites><orcidid>0000-0001-8645-5505 ; 0000-0001-6661-6324 ; 0000-0002-4226-1853</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Yuan, Jin-Wei</creatorcontrib><creatorcontrib>Shen, Lu</creatorcontrib><creatorcontrib>Ma, Meng-Yao</creatorcontrib><creatorcontrib>Feng, Shi</creatorcontrib><creatorcontrib>Yang, Wan</creatorcontrib><creatorcontrib>Yang, Liang-Ru</creatorcontrib><creatorcontrib>Xiao, Yong-Mei</creatorcontrib><creatorcontrib>Zhang, Shou-Ren</creatorcontrib><creatorcontrib>Qu, Ling-Bo</creatorcontrib><title>Visible-light-induced tandem difluoroalkylated spirocyclization of N -arylpropiolamides: access to C3-difluoroacetylated spiro[4,5]trienones</title><title>New journal of chemistry</title><description>A visible-light-catalyzed difluoroacetylated spirocyclization of
N
-arylpropiolamides with ethyl bromodifluoroacetate as a CF
2
CO
2
Et radical precursor is described. This approach allows the formation of two carbon–carbon bonds and one carbon–oxygen bond in a single reaction through a sequence of C–H oxidative coupling,
ipso
-cyclization and dearomatization processes. This protocol affords a straightforward route to synthesize CF
2
CO
2
Et-containing spiro[4.5]trienones in moderate to good yields.</description><subject>Carbon</subject><subject>Covalent bonds</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpNkM1OAyEUhYnRxFrd-AQk7owoDDBT3JnW35i6UTfGTBgGlEqHEZhFfQYfWkyNuronuSffvecAsE_wMcFUnMyK-Q3GhJLZBhgRWgokipJsZk0YQ5izchvsxLjIHlKVZAQ-H220jdPI2ZfXhGzXDkq3MMmu1UvYWuMGH7x0bysnU17E3gavVsrZD5ms76A3cA6RDCvXB99b7-TStjqeQqmUjhEmD6cU_YKUTv9JT-yIP6dgdec7HXfBlpEu6r2fOQYPF-f30yt0e3d5PT27RargIiEptFRCipI1E25k0WjVSlwZRrTilCtRMYEZwzn5pBGVoc1E0UZJTTQ2ihs6Bgdrbn75fdAx1Qs_hC6frIuSMkIpLXh2Ha5dKvgYgzZ1H-wyJ60Jrr_brv_apl8dc3Xl</recordid><startdate>20220228</startdate><enddate>20220228</enddate><creator>Yuan, Jin-Wei</creator><creator>Shen, Lu</creator><creator>Ma, Meng-Yao</creator><creator>Feng, Shi</creator><creator>Yang, Wan</creator><creator>Yang, Liang-Ru</creator><creator>Xiao, Yong-Mei</creator><creator>Zhang, Shou-Ren</creator><creator>Qu, Ling-Bo</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0001-8645-5505</orcidid><orcidid>https://orcid.org/0000-0001-6661-6324</orcidid><orcidid>https://orcid.org/0000-0002-4226-1853</orcidid></search><sort><creationdate>20220228</creationdate><title>Visible-light-induced tandem difluoroalkylated spirocyclization of N -arylpropiolamides: access to C3-difluoroacetylated spiro[4,5]trienones</title><author>Yuan, Jin-Wei ; Shen, Lu ; Ma, Meng-Yao ; Feng, Shi ; Yang, Wan ; Yang, Liang-Ru ; Xiao, Yong-Mei ; Zhang, Shou-Ren ; Qu, Ling-Bo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-a9eac9a964b85fa2becda07f41ec535c974904402618b97f3b8c3bcae1e0fc5f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Carbon</topic><topic>Covalent bonds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yuan, Jin-Wei</creatorcontrib><creatorcontrib>Shen, Lu</creatorcontrib><creatorcontrib>Ma, Meng-Yao</creatorcontrib><creatorcontrib>Feng, Shi</creatorcontrib><creatorcontrib>Yang, Wan</creatorcontrib><creatorcontrib>Yang, Liang-Ru</creatorcontrib><creatorcontrib>Xiao, Yong-Mei</creatorcontrib><creatorcontrib>Zhang, Shou-Ren</creatorcontrib><creatorcontrib>Qu, Ling-Bo</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yuan, Jin-Wei</au><au>Shen, Lu</au><au>Ma, Meng-Yao</au><au>Feng, Shi</au><au>Yang, Wan</au><au>Yang, Liang-Ru</au><au>Xiao, Yong-Mei</au><au>Zhang, Shou-Ren</au><au>Qu, Ling-Bo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Visible-light-induced tandem difluoroalkylated spirocyclization of N -arylpropiolamides: access to C3-difluoroacetylated spiro[4,5]trienones</atitle><jtitle>New journal of chemistry</jtitle><date>2022-02-28</date><risdate>2022</risdate><volume>46</volume><issue>9</issue><spage>4470</spage><epage>4482</epage><pages>4470-4482</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>A visible-light-catalyzed difluoroacetylated spirocyclization of
N
-arylpropiolamides with ethyl bromodifluoroacetate as a CF
2
CO
2
Et radical precursor is described. This approach allows the formation of two carbon–carbon bonds and one carbon–oxygen bond in a single reaction through a sequence of C–H oxidative coupling,
ipso
-cyclization and dearomatization processes. This protocol affords a straightforward route to synthesize CF
2
CO
2
Et-containing spiro[4.5]trienones in moderate to good yields.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D2NJ00131D</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0001-8645-5505</orcidid><orcidid>https://orcid.org/0000-0001-6661-6324</orcidid><orcidid>https://orcid.org/0000-0002-4226-1853</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1144-0546 |
| ispartof | New journal of chemistry, 2022-02, Vol.46 (9), p.4470-4482 |
| issn | 1144-0546 1369-9261 |
| language | eng |
| recordid | cdi_proquest_journals_2634133325 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Carbon Covalent bonds |
| title | Visible-light-induced tandem difluoroalkylated spirocyclization of N -arylpropiolamides: access to C3-difluoroacetylated spiro[4,5]trienones |
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