Visible-Light Photoredox-Catalyzed Formal [5 + 1] Cycloaddition of N‑Tosyl Vinylaziridines with Difluoroalkyl Halides

A visible-light photoredox-catalyzed formal [5 + 1] cycloaddition of N-tosyl vinylaziridines with difluoroalkyl halides as unique C1 synthons was developed. The procedure provides an efficient and practical method to synthesize diverse pyridines in moderate to good yields. The reaction underwent a r...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2020-12, Vol.22 (24), p.9658-9664
Main Authors: Liu, Yantao, Luo, Wen, Wang, Zhenjie, Zhao, Yuxin, Zhao, Jingjing, Xu, Xuejun, Wang, Chaojie, Li, Pan
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a345t-e7a2c78321232ae5d8ced4e17912850cb415923a38e4cb85d3436465d19c11283
cites cdi_FETCH-LOGICAL-a345t-e7a2c78321232ae5d8ced4e17912850cb415923a38e4cb85d3436465d19c11283
container_end_page 9664
container_issue 24
container_start_page 9658
container_title Organic letters
container_volume 22
creator Liu, Yantao
Luo, Wen
Wang, Zhenjie
Zhao, Yuxin
Zhao, Jingjing
Xu, Xuejun
Wang, Chaojie
Li, Pan
description A visible-light photoredox-catalyzed formal [5 + 1] cycloaddition of N-tosyl vinylaziridines with difluoroalkyl halides as unique C1 synthons was developed. The procedure provides an efficient and practical method to synthesize diverse pyridines in moderate to good yields. The reaction underwent a radical-initiated kinetically controlled ring-opening of vinylaziridines and involved a key α,β-unsaturated imine intermediate, followed by an E2 elimination, a 6π electrocyclization, and defluorinated aromatization.
doi_str_mv 10.1021/acs.orglett.0c03718
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2464188714</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2464188714</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-e7a2c78321232ae5d8ced4e17912850cb415923a38e4cb85d3436465d19c11283</originalsourceid><addsrcrecordid>eNp9kEtOHDEQhi2UiPcJkCIvI0U9uPzoxxJNAkQaERbAJopaHruGMXjaYLtFmlWukCvmJDSaCUtWVSp9f5XqI-QI2AQYh2Nt0iTEW485T5hhooJ6i-yC4qKomOIf3vqS7ZC9lO4Yg3HSbJMdIbgoGxC75OnGJTf3WMzc7TLTy2XIIaINv4upztoPz2jpaYgr7elPRb9Q-EWng_FBW-uyCx0NC3rx78_fq5AGT29cN3j97KKzrsNEn1xe0q9u4fsQg_b3I3KuvbOYDsjHhfYJDzd1n1yffruanhezH2ffpyezQgupcoGV5qaqBQcuuEZla4NWIlQN8FoxM5egGi60qFGaea2skKKUpbLQGBgRsU8-r_c-xPDYY8rtyiWD3usOQ59aLksJdV2BHFGxRk0MKUVctA_RrXQcWmDtq_F2NN5ujLcb42Pq0-ZAP1-hfcv8VzwCx2vgNX0X-tiN_7678gXxSJDC</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2464188714</pqid></control><display><type>article</type><title>Visible-Light Photoredox-Catalyzed Formal [5 + 1] Cycloaddition of N‑Tosyl Vinylaziridines with Difluoroalkyl Halides</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Liu, Yantao ; Luo, Wen ; Wang, Zhenjie ; Zhao, Yuxin ; Zhao, Jingjing ; Xu, Xuejun ; Wang, Chaojie ; Li, Pan</creator><creatorcontrib>Liu, Yantao ; Luo, Wen ; Wang, Zhenjie ; Zhao, Yuxin ; Zhao, Jingjing ; Xu, Xuejun ; Wang, Chaojie ; Li, Pan</creatorcontrib><description>A visible-light photoredox-catalyzed formal [5 + 1] cycloaddition of N-tosyl vinylaziridines with difluoroalkyl halides as unique C1 synthons was developed. The procedure provides an efficient and practical method to synthesize diverse pyridines in moderate to good yields. The reaction underwent a radical-initiated kinetically controlled ring-opening of vinylaziridines and involved a key α,β-unsaturated imine intermediate, followed by an E2 elimination, a 6π electrocyclization, and defluorinated aromatization.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.0c03718</identifier><identifier>PMID: 33236913</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2020-12, Vol.22 (24), p.9658-9664</ispartof><rights>2020 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-e7a2c78321232ae5d8ced4e17912850cb415923a38e4cb85d3436465d19c11283</citedby><cites>FETCH-LOGICAL-a345t-e7a2c78321232ae5d8ced4e17912850cb415923a38e4cb85d3436465d19c11283</cites><orcidid>0000-0001-6782-0650 ; 0000-0001-6658-9207</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33236913$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Yantao</creatorcontrib><creatorcontrib>Luo, Wen</creatorcontrib><creatorcontrib>Wang, Zhenjie</creatorcontrib><creatorcontrib>Zhao, Yuxin</creatorcontrib><creatorcontrib>Zhao, Jingjing</creatorcontrib><creatorcontrib>Xu, Xuejun</creatorcontrib><creatorcontrib>Wang, Chaojie</creatorcontrib><creatorcontrib>Li, Pan</creatorcontrib><title>Visible-Light Photoredox-Catalyzed Formal [5 + 1] Cycloaddition of N‑Tosyl Vinylaziridines with Difluoroalkyl Halides</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A visible-light photoredox-catalyzed formal [5 + 1] cycloaddition of N-tosyl vinylaziridines with difluoroalkyl halides as unique C1 synthons was developed. The procedure provides an efficient and practical method to synthesize diverse pyridines in moderate to good yields. The reaction underwent a radical-initiated kinetically controlled ring-opening of vinylaziridines and involved a key α,β-unsaturated imine intermediate, followed by an E2 elimination, a 6π electrocyclization, and defluorinated aromatization.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kEtOHDEQhi2UiPcJkCIvI0U9uPzoxxJNAkQaERbAJopaHruGMXjaYLtFmlWukCvmJDSaCUtWVSp9f5XqI-QI2AQYh2Nt0iTEW485T5hhooJ6i-yC4qKomOIf3vqS7ZC9lO4Yg3HSbJMdIbgoGxC75OnGJTf3WMzc7TLTy2XIIaINv4upztoPz2jpaYgr7elPRb9Q-EWng_FBW-uyCx0NC3rx78_fq5AGT29cN3j97KKzrsNEn1xe0q9u4fsQg_b3I3KuvbOYDsjHhfYJDzd1n1yffruanhezH2ffpyezQgupcoGV5qaqBQcuuEZla4NWIlQN8FoxM5egGi60qFGaea2skKKUpbLQGBgRsU8-r_c-xPDYY8rtyiWD3usOQ59aLksJdV2BHFGxRk0MKUVctA_RrXQcWmDtq_F2NN5ujLcb42Pq0-ZAP1-hfcv8VzwCx2vgNX0X-tiN_7678gXxSJDC</recordid><startdate>20201218</startdate><enddate>20201218</enddate><creator>Liu, Yantao</creator><creator>Luo, Wen</creator><creator>Wang, Zhenjie</creator><creator>Zhao, Yuxin</creator><creator>Zhao, Jingjing</creator><creator>Xu, Xuejun</creator><creator>Wang, Chaojie</creator><creator>Li, Pan</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6782-0650</orcidid><orcidid>https://orcid.org/0000-0001-6658-9207</orcidid></search><sort><creationdate>20201218</creationdate><title>Visible-Light Photoredox-Catalyzed Formal [5 + 1] Cycloaddition of N‑Tosyl Vinylaziridines with Difluoroalkyl Halides</title><author>Liu, Yantao ; Luo, Wen ; Wang, Zhenjie ; Zhao, Yuxin ; Zhao, Jingjing ; Xu, Xuejun ; Wang, Chaojie ; Li, Pan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-e7a2c78321232ae5d8ced4e17912850cb415923a38e4cb85d3436465d19c11283</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Yantao</creatorcontrib><creatorcontrib>Luo, Wen</creatorcontrib><creatorcontrib>Wang, Zhenjie</creatorcontrib><creatorcontrib>Zhao, Yuxin</creatorcontrib><creatorcontrib>Zhao, Jingjing</creatorcontrib><creatorcontrib>Xu, Xuejun</creatorcontrib><creatorcontrib>Wang, Chaojie</creatorcontrib><creatorcontrib>Li, Pan</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Yantao</au><au>Luo, Wen</au><au>Wang, Zhenjie</au><au>Zhao, Yuxin</au><au>Zhao, Jingjing</au><au>Xu, Xuejun</au><au>Wang, Chaojie</au><au>Li, Pan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Visible-Light Photoredox-Catalyzed Formal [5 + 1] Cycloaddition of N‑Tosyl Vinylaziridines with Difluoroalkyl Halides</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2020-12-18</date><risdate>2020</risdate><volume>22</volume><issue>24</issue><spage>9658</spage><epage>9664</epage><pages>9658-9664</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A visible-light photoredox-catalyzed formal [5 + 1] cycloaddition of N-tosyl vinylaziridines with difluoroalkyl halides as unique C1 synthons was developed. The procedure provides an efficient and practical method to synthesize diverse pyridines in moderate to good yields. The reaction underwent a radical-initiated kinetically controlled ring-opening of vinylaziridines and involved a key α,β-unsaturated imine intermediate, followed by an E2 elimination, a 6π electrocyclization, and defluorinated aromatization.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>33236913</pmid><doi>10.1021/acs.orglett.0c03718</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-6782-0650</orcidid><orcidid>https://orcid.org/0000-0001-6658-9207</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2020-12, Vol.22 (24), p.9658-9664
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2464188714
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Visible-Light Photoredox-Catalyzed Formal [5 + 1] Cycloaddition of N‑Tosyl Vinylaziridines with Difluoroalkyl Halides
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T23%3A57%3A49IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Visible-Light%20Photoredox-Catalyzed%20Formal%20%5B5%20+%201%5D%20Cycloaddition%20of%20N%E2%80%91Tosyl%20Vinylaziridines%20with%20Difluoroalkyl%20Halides&rft.jtitle=Organic%20letters&rft.au=Liu,%20Yantao&rft.date=2020-12-18&rft.volume=22&rft.issue=24&rft.spage=9658&rft.epage=9664&rft.pages=9658-9664&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.0c03718&rft_dat=%3Cproquest_cross%3E2464188714%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a345t-e7a2c78321232ae5d8ced4e17912850cb415923a38e4cb85d3436465d19c11283%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2464188714&rft_id=info:pmid/33236913&rfr_iscdi=true