Photocatalytic synthesis of azaheterocycle-fused piperidines and pyrrolidines via tandem difunctionalization of unactivated alkenes
A variety of azaheterocycle-fused piperidines and pyrrolidines bearing CF and CHF functionalities were obtained using CF SO Na and CHF SO Na by visible light photocatalysis. This protocol involves a radical cascade cyclization tandem tri- and difluoromethylation-arylation of pendent unactivated alke...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2023-04, Vol.21 (16), p.3317-3322 |
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| container_title | Organic & biomolecular chemistry |
| container_volume | 21 |
| creator | Zhou, Qun-Huai Dai, Jia-Ying Zhao, Wen-Jing Zhong, Xi-Ya Liu, Chun-Yang Luo, Wei-Wei Li, Zhi-Wei Li, Jiang-Sheng Liu, Wei-Dong |
| description | A variety of azaheterocycle-fused piperidines and pyrrolidines bearing CF
and CHF
functionalities were obtained using CF
SO
Na and CHF
SO
Na by visible light photocatalysis. This protocol involves a radical cascade cyclization
tandem tri- and difluoromethylation-arylation of pendent unactivated alkenes. Benzimidazole, imidazole, theophylline, purine, and indole serve as applicable anchors, thereby enriching the structural diversity of piperidine and pyrrolidine derivatives. This method features mild, additive-free and transition metal-free conditions. |
| doi_str_mv | 10.1039/d3ob00241a |
| format | Article |
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and CHF
functionalities were obtained using CF
SO
Na and CHF
SO
Na by visible light photocatalysis. This protocol involves a radical cascade cyclization
tandem tri- and difluoromethylation-arylation of pendent unactivated alkenes. Benzimidazole, imidazole, theophylline, purine, and indole serve as applicable anchors, thereby enriching the structural diversity of piperidine and pyrrolidine derivatives. This method features mild, additive-free and transition metal-free conditions.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d3ob00241a</identifier><identifier>PMID: 37009653</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkenes ; Benzimidazoles ; Imidazole ; Photocatalysis ; Piperidine ; Pyrrolidine ; Theophylline ; Transition metals</subject><ispartof>Organic & biomolecular chemistry, 2023-04, Vol.21 (16), p.3317-3322</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c315t-79e91b54108e37a610c9bd130c486ee987e654ed76a2256ea475879b6950fde13</citedby><cites>FETCH-LOGICAL-c315t-79e91b54108e37a610c9bd130c486ee987e654ed76a2256ea475879b6950fde13</cites><orcidid>0000-0001-8359-4120</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37009653$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhou, Qun-Huai</creatorcontrib><creatorcontrib>Dai, Jia-Ying</creatorcontrib><creatorcontrib>Zhao, Wen-Jing</creatorcontrib><creatorcontrib>Zhong, Xi-Ya</creatorcontrib><creatorcontrib>Liu, Chun-Yang</creatorcontrib><creatorcontrib>Luo, Wei-Wei</creatorcontrib><creatorcontrib>Li, Zhi-Wei</creatorcontrib><creatorcontrib>Li, Jiang-Sheng</creatorcontrib><creatorcontrib>Liu, Wei-Dong</creatorcontrib><title>Photocatalytic synthesis of azaheterocycle-fused piperidines and pyrrolidines via tandem difunctionalization of unactivated alkenes</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>A variety of azaheterocycle-fused piperidines and pyrrolidines bearing CF
and CHF
functionalities were obtained using CF
SO
Na and CHF
SO
Na by visible light photocatalysis. This protocol involves a radical cascade cyclization
tandem tri- and difluoromethylation-arylation of pendent unactivated alkenes. Benzimidazole, imidazole, theophylline, purine, and indole serve as applicable anchors, thereby enriching the structural diversity of piperidine and pyrrolidine derivatives. This method features mild, additive-free and transition metal-free conditions.</description><subject>Alkenes</subject><subject>Benzimidazoles</subject><subject>Imidazole</subject><subject>Photocatalysis</subject><subject>Piperidine</subject><subject>Pyrrolidine</subject><subject>Theophylline</subject><subject>Transition metals</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkUFP3DAQha2KqlDaS38AisSlQgqM49iOj0Bpi4QEh_YcTZyJ1jQbL7aDFK788XrLlgOnefP0zZNGj7EvHE45CHPWC98BVDXHd-yA11qXIIXZe9UV7LOPMd4DcKNV_YHtCw1glBQH7Plu5ZO3mHBckrNFXKa0ouhi4YcCn3BFiYK3ix2pHOZIfbFxGwqudxPFAqe8LyH4cWc8OixSdmld9G6YJ5ucn3B0T7gV28x5wmw-YspROP6hfPWJvR9wjPR5Nw_Z7-9Xvy5_lje3P64vz29KK7hMpTZkeCdrDg0JjYqDNV3PBdi6UUSm0aRkTb1WWFVSEdZaNtp0ykgYeuLikH19yd0E_zBTTO3aRUvjiBP5ObaVNrUyVcYzevwGvfdzyJ9kqgHZSM1BZerkhbLBxxhoaDfBrTEsLYd2W037Tdxe_KvmPMNHu8i5W1P_iv7vQvwFf76L2w</recordid><startdate>20230426</startdate><enddate>20230426</enddate><creator>Zhou, Qun-Huai</creator><creator>Dai, Jia-Ying</creator><creator>Zhao, Wen-Jing</creator><creator>Zhong, Xi-Ya</creator><creator>Liu, Chun-Yang</creator><creator>Luo, Wei-Wei</creator><creator>Li, Zhi-Wei</creator><creator>Li, Jiang-Sheng</creator><creator>Liu, Wei-Dong</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/0000-0001-8359-4120</orcidid></search><sort><creationdate>20230426</creationdate><title>Photocatalytic synthesis of azaheterocycle-fused piperidines and pyrrolidines via tandem difunctionalization of unactivated alkenes</title><author>Zhou, Qun-Huai ; Dai, Jia-Ying ; Zhao, Wen-Jing ; Zhong, Xi-Ya ; Liu, Chun-Yang ; Luo, Wei-Wei ; Li, Zhi-Wei ; Li, Jiang-Sheng ; Liu, Wei-Dong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c315t-79e91b54108e37a610c9bd130c486ee987e654ed76a2256ea475879b6950fde13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Alkenes</topic><topic>Benzimidazoles</topic><topic>Imidazole</topic><topic>Photocatalysis</topic><topic>Piperidine</topic><topic>Pyrrolidine</topic><topic>Theophylline</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhou, Qun-Huai</creatorcontrib><creatorcontrib>Dai, Jia-Ying</creatorcontrib><creatorcontrib>Zhao, Wen-Jing</creatorcontrib><creatorcontrib>Zhong, Xi-Ya</creatorcontrib><creatorcontrib>Liu, Chun-Yang</creatorcontrib><creatorcontrib>Luo, Wei-Wei</creatorcontrib><creatorcontrib>Li, Zhi-Wei</creatorcontrib><creatorcontrib>Li, Jiang-Sheng</creatorcontrib><creatorcontrib>Liu, Wei-Dong</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>Zhou, Qun-Huai</au><au>Dai, Jia-Ying</au><au>Zhao, Wen-Jing</au><au>Zhong, Xi-Ya</au><au>Liu, Chun-Yang</au><au>Luo, Wei-Wei</au><au>Li, Zhi-Wei</au><au>Li, Jiang-Sheng</au><au>Liu, Wei-Dong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photocatalytic synthesis of azaheterocycle-fused piperidines and pyrrolidines via tandem difunctionalization of unactivated alkenes</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2023-04-26</date><risdate>2023</risdate><volume>21</volume><issue>16</issue><spage>3317</spage><epage>3322</epage><pages>3317-3322</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A variety of azaheterocycle-fused piperidines and pyrrolidines bearing CF
and CHF
functionalities were obtained using CF
SO
Na and CHF
SO
Na by visible light photocatalysis. This protocol involves a radical cascade cyclization
tandem tri- and difluoromethylation-arylation of pendent unactivated alkenes. Benzimidazole, imidazole, theophylline, purine, and indole serve as applicable anchors, thereby enriching the structural diversity of piperidine and pyrrolidine derivatives. This method features mild, additive-free and transition metal-free conditions.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>37009653</pmid><doi>10.1039/d3ob00241a</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-8359-4120</orcidid></addata></record> |
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| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2023-04, Vol.21 (16), p.3317-3322 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2794692950 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alkenes Benzimidazoles Imidazole Photocatalysis Piperidine Pyrrolidine Theophylline Transition metals |
| title | Photocatalytic synthesis of azaheterocycle-fused piperidines and pyrrolidines via tandem difunctionalization of unactivated alkenes |
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