Trichloromethylative Olefin Cycloamination by Photoredox Catalysis
The trichloromethyl group is an important functionality. It is a useful synthetic moiety and appears in the structures of natural and biologically active compounds; hence, developing synthetic methods for its introduction into structural motifs is an important objective. Herein, we report an efficie...
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Veröffentlicht in: | European journal of organic chemistry 2021-08, Vol.2021 (32), p.4531-4535 |
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creator | Harada, Shinji Masuda, Ryuya Morikawa, Takahiro Nishida, Atsushi |
description | The trichloromethyl group is an important functionality. It is a useful synthetic moiety and appears in the structures of natural and biologically active compounds; hence, developing synthetic methods for its introduction into structural motifs is an important objective. Herein, we report an efficient chemistry for the trichloromethylations and cycloaminations of olefin. These reactions are realized in a single step and triggered by the addition of the trichloromethyl radical, generated from bromotrichloromethane by photoredox catalysis, to a double bond, with the resulting intermediate trapped through intramolecular reaction with an amino group. This process facilitates the construction of N‐heterocycles having trichloromethyl units and tetrasubstituted carbons from simple compounds under mild conditions.
The trichloromethyl group is an important functionality as it appears in the structures of biologically active compounds. The trichloromethylative olefin cycloaminations are reported. These reactions are triggered by the addition of the trichloromethyl radical, generated from bromotrichloromethane by photoredox catalysis, to a double bond. This process facilitates the construction of N‐heterocycles having trichloromethyl units. |
doi_str_mv | 10.1002/ejoc.202100898 |
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The trichloromethyl group is an important functionality as it appears in the structures of biologically active compounds. The trichloromethylative olefin cycloaminations are reported. These reactions are triggered by the addition of the trichloromethyl radical, generated from bromotrichloromethane by photoredox catalysis, to a double bond. This process facilitates the construction of N‐heterocycles having trichloromethyl units.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202100898</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkenes ; Catalysis ; Cyclization ; Heterocycles ; Photocatalysis ; Photoredox catalysis ; Trichloromethyl</subject><ispartof>European journal of organic chemistry, 2021-08, Vol.2021 (32), p.4531-4535</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3838-a26cdb0d41f75c3726f8e42debf01e2fb43100232a270396a3faeafd1f2ee7123</citedby><cites>FETCH-LOGICAL-c3838-a26cdb0d41f75c3726f8e42debf01e2fb43100232a270396a3faeafd1f2ee7123</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.202100898$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202100898$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27923,27924,45573,45574</link.rule.ids></links><search><creatorcontrib>Harada, Shinji</creatorcontrib><creatorcontrib>Masuda, Ryuya</creatorcontrib><creatorcontrib>Morikawa, Takahiro</creatorcontrib><creatorcontrib>Nishida, Atsushi</creatorcontrib><title>Trichloromethylative Olefin Cycloamination by Photoredox Catalysis</title><title>European journal of organic chemistry</title><description>The trichloromethyl group is an important functionality. It is a useful synthetic moiety and appears in the structures of natural and biologically active compounds; hence, developing synthetic methods for its introduction into structural motifs is an important objective. Herein, we report an efficient chemistry for the trichloromethylations and cycloaminations of olefin. These reactions are realized in a single step and triggered by the addition of the trichloromethyl radical, generated from bromotrichloromethane by photoredox catalysis, to a double bond, with the resulting intermediate trapped through intramolecular reaction with an amino group. This process facilitates the construction of N‐heterocycles having trichloromethyl units and tetrasubstituted carbons from simple compounds under mild conditions.
The trichloromethyl group is an important functionality as it appears in the structures of biologically active compounds. The trichloromethylative olefin cycloaminations are reported. These reactions are triggered by the addition of the trichloromethyl radical, generated from bromotrichloromethane by photoredox catalysis, to a double bond. This process facilitates the construction of N‐heterocycles having trichloromethyl units.</description><subject>Alkenes</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>Heterocycles</subject><subject>Photocatalysis</subject><subject>Photoredox catalysis</subject><subject>Trichloromethyl</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkL1PwzAQxS0EEqWwMkdiTjnbqROPEJUCqlSGIrFZTnJWXblxsVMg_z2pimBkug_93j3dI-SawoQCsFvc-HrCgA1DIYsTMqIgZQpCwunQZzxLqeRv5-Qixg0ASCHoiNyvgq3Xzge_xW7dO93ZD0yWDo1tk7Kvnddb2w5b3yZVn7ysfecDNv4rKXWnXR9tvCRnRruIVz91TF4fZqvyMV0s50_l3SKtecGLVDNRNxU0GTX5tOY5E6bAjDVYGaDITJXxwxucaZYDl0Jzo1GbhhqGmFPGx-TmeHcX_PseY6c2fh_awVKxqcimnFNJB2pypOrgYwxo1C7YrQ69oqAOBuqQk_rNaRDIo-DTOuz_odXseVn-ab8B2BltTA</recordid><startdate>20210826</startdate><enddate>20210826</enddate><creator>Harada, Shinji</creator><creator>Masuda, Ryuya</creator><creator>Morikawa, Takahiro</creator><creator>Nishida, Atsushi</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20210826</creationdate><title>Trichloromethylative Olefin Cycloamination by Photoredox Catalysis</title><author>Harada, Shinji ; Masuda, Ryuya ; Morikawa, Takahiro ; Nishida, Atsushi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3838-a26cdb0d41f75c3726f8e42debf01e2fb43100232a270396a3faeafd1f2ee7123</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alkenes</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>Heterocycles</topic><topic>Photocatalysis</topic><topic>Photoredox catalysis</topic><topic>Trichloromethyl</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Harada, Shinji</creatorcontrib><creatorcontrib>Masuda, Ryuya</creatorcontrib><creatorcontrib>Morikawa, Takahiro</creatorcontrib><creatorcontrib>Nishida, Atsushi</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Harada, Shinji</au><au>Masuda, Ryuya</au><au>Morikawa, Takahiro</au><au>Nishida, Atsushi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Trichloromethylative Olefin Cycloamination by Photoredox Catalysis</atitle><jtitle>European journal of organic chemistry</jtitle><date>2021-08-26</date><risdate>2021</risdate><volume>2021</volume><issue>32</issue><spage>4531</spage><epage>4535</epage><pages>4531-4535</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The trichloromethyl group is an important functionality. It is a useful synthetic moiety and appears in the structures of natural and biologically active compounds; hence, developing synthetic methods for its introduction into structural motifs is an important objective. Herein, we report an efficient chemistry for the trichloromethylations and cycloaminations of olefin. These reactions are realized in a single step and triggered by the addition of the trichloromethyl radical, generated from bromotrichloromethane by photoredox catalysis, to a double bond, with the resulting intermediate trapped through intramolecular reaction with an amino group. This process facilitates the construction of N‐heterocycles having trichloromethyl units and tetrasubstituted carbons from simple compounds under mild conditions.
The trichloromethyl group is an important functionality as it appears in the structures of biologically active compounds. The trichloromethylative olefin cycloaminations are reported. These reactions are triggered by the addition of the trichloromethyl radical, generated from bromotrichloromethane by photoredox catalysis, to a double bond. This process facilitates the construction of N‐heterocycles having trichloromethyl units.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202100898</doi><tpages>5</tpages></addata></record> |
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subjects | Alkenes Catalysis Cyclization Heterocycles Photocatalysis Photoredox catalysis Trichloromethyl |
title | Trichloromethylative Olefin Cycloamination by Photoredox Catalysis |
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