Synthesis of 2,4,6-Trisubstituted Pyridines by Oxidative Eosin Y Photoredox Catalysis

Eosin Y, an organic dye, was activated as a photoredox catalyst in the presence of molecular oxygen using visible light and, when it was used in the reaction of aryl ketones and benzyl amines, afforded good yields (52–87%) of 2,4,6-triarylpyridines (21 examples) at ambient temperature. The aryl grou...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2016-08, Vol.81 (16), p.7121-7126
Main Authors: Rohokale, Rajendra S, Koenig, Burkhard, Dhavale, Dilip D
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-a399t-6f5fec778442930564db82a32b7a61dfbf2baa301b24afde9cc6ab41800a1cb23
cites cdi_FETCH-LOGICAL-a399t-6f5fec778442930564db82a32b7a61dfbf2baa301b24afde9cc6ab41800a1cb23
container_end_page 7126
container_issue 16
container_start_page 7121
container_title Journal of organic chemistry
container_volume 81
creator Rohokale, Rajendra S
Koenig, Burkhard
Dhavale, Dilip D
description Eosin Y, an organic dye, was activated as a photoredox catalyst in the presence of molecular oxygen using visible light and, when it was used in the reaction of aryl ketones and benzyl amines, afforded good yields (52–87%) of 2,4,6-triarylpyridines (21 examples) at ambient temperature. The aryl groups at the 2- and 6-positions are derived from ketones, while benzyl amine plays the dual role of providing an aryl functionality at the 4-position of pyridine as well as being a nitrogen donor.
doi_str_mv 10.1021/acs.joc.6b00979
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1812884130</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1812884130</sourcerecordid><originalsourceid>FETCH-LOGICAL-a399t-6f5fec778442930564db82a32b7a61dfbf2baa301b24afde9cc6ab41800a1cb23</originalsourceid><addsrcrecordid>eNp1kM9LwzAUgIMobk7P3iRHwXXLr6btUcb8AYMN3A6eQtKkLGNrNEll_e-tdHrzXd7lex-8D4BbjCYYETyVZZjsXDnhCqEiK87AEKcEJbxA7BwMESIkoYTTAbgKYYe6SdP0EgxIRjnJGB-CzVtbx60JNkBXQTJmY56svQ2NCtHGJhoNV6232tYmQNXC5dFqGe2XgXMXbA3f4WrrovNGuyOcySj3bee6BheV3Adzc9ojsHmar2cvyWL5_Dp7XCSSFkVMeJVWpsyynDFSUJRyplVOJCUqkxzrSlVESUkRVoTJSpuiLLlUDOcISVwqQkfgvvd-ePfZmBDFwYbS7PeyNq4JAueY5DnDFHXotEdL70LwphIf3h6kbwVG4qel6FqKrqU4tewu7k7yRh2M_uN_43XAQw_0l42vu1__1X0Dg3F_lg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1812884130</pqid></control><display><type>article</type><title>Synthesis of 2,4,6-Trisubstituted Pyridines by Oxidative Eosin Y Photoredox Catalysis</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Rohokale, Rajendra S ; Koenig, Burkhard ; Dhavale, Dilip D</creator><creatorcontrib>Rohokale, Rajendra S ; Koenig, Burkhard ; Dhavale, Dilip D</creatorcontrib><description>Eosin Y, an organic dye, was activated as a photoredox catalyst in the presence of molecular oxygen using visible light and, when it was used in the reaction of aryl ketones and benzyl amines, afforded good yields (52–87%) of 2,4,6-triarylpyridines (21 examples) at ambient temperature. The aryl groups at the 2- and 6-positions are derived from ketones, while benzyl amine plays the dual role of providing an aryl functionality at the 4-position of pyridine as well as being a nitrogen donor.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.6b00979</identifier><identifier>PMID: 27362746</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2016-08, Vol.81 (16), p.7121-7126</ispartof><rights>Copyright © 2016 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a399t-6f5fec778442930564db82a32b7a61dfbf2baa301b24afde9cc6ab41800a1cb23</citedby><cites>FETCH-LOGICAL-a399t-6f5fec778442930564db82a32b7a61dfbf2baa301b24afde9cc6ab41800a1cb23</cites></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/27362746$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rohokale, Rajendra S</creatorcontrib><creatorcontrib>Koenig, Burkhard</creatorcontrib><creatorcontrib>Dhavale, Dilip D</creatorcontrib><title>Synthesis of 2,4,6-Trisubstituted Pyridines by Oxidative Eosin Y Photoredox Catalysis</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Eosin Y, an organic dye, was activated as a photoredox catalyst in the presence of molecular oxygen using visible light and, when it was used in the reaction of aryl ketones and benzyl amines, afforded good yields (52–87%) of 2,4,6-triarylpyridines (21 examples) at ambient temperature. The aryl groups at the 2- and 6-positions are derived from ketones, while benzyl amine plays the dual role of providing an aryl functionality at the 4-position of pyridine as well as being a nitrogen donor.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp1kM9LwzAUgIMobk7P3iRHwXXLr6btUcb8AYMN3A6eQtKkLGNrNEll_e-tdHrzXd7lex-8D4BbjCYYETyVZZjsXDnhCqEiK87AEKcEJbxA7BwMESIkoYTTAbgKYYe6SdP0EgxIRjnJGB-CzVtbx60JNkBXQTJmY56svQ2NCtHGJhoNV6232tYmQNXC5dFqGe2XgXMXbA3f4WrrovNGuyOcySj3bee6BheV3Adzc9ojsHmar2cvyWL5_Dp7XCSSFkVMeJVWpsyynDFSUJRyplVOJCUqkxzrSlVESUkRVoTJSpuiLLlUDOcISVwqQkfgvvd-ePfZmBDFwYbS7PeyNq4JAueY5DnDFHXotEdL70LwphIf3h6kbwVG4qel6FqKrqU4tewu7k7yRh2M_uN_43XAQw_0l42vu1__1X0Dg3F_lg</recordid><startdate>20160819</startdate><enddate>20160819</enddate><creator>Rohokale, Rajendra S</creator><creator>Koenig, Burkhard</creator><creator>Dhavale, Dilip D</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20160819</creationdate><title>Synthesis of 2,4,6-Trisubstituted Pyridines by Oxidative Eosin Y Photoredox Catalysis</title><author>Rohokale, Rajendra S ; Koenig, Burkhard ; Dhavale, Dilip D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a399t-6f5fec778442930564db82a32b7a61dfbf2baa301b24afde9cc6ab41800a1cb23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rohokale, Rajendra S</creatorcontrib><creatorcontrib>Koenig, Burkhard</creatorcontrib><creatorcontrib>Dhavale, Dilip D</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rohokale, Rajendra S</au><au>Koenig, Burkhard</au><au>Dhavale, Dilip D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 2,4,6-Trisubstituted Pyridines by Oxidative Eosin Y Photoredox Catalysis</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2016-08-19</date><risdate>2016</risdate><volume>81</volume><issue>16</issue><spage>7121</spage><epage>7126</epage><pages>7121-7126</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Eosin Y, an organic dye, was activated as a photoredox catalyst in the presence of molecular oxygen using visible light and, when it was used in the reaction of aryl ketones and benzyl amines, afforded good yields (52–87%) of 2,4,6-triarylpyridines (21 examples) at ambient temperature. The aryl groups at the 2- and 6-positions are derived from ketones, while benzyl amine plays the dual role of providing an aryl functionality at the 4-position of pyridine as well as being a nitrogen donor.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>27362746</pmid><doi>10.1021/acs.joc.6b00979</doi><tpages>6</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2016-08, Vol.81 (16), p.7121-7126
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_1812884130
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Synthesis of 2,4,6-Trisubstituted Pyridines by Oxidative Eosin Y Photoredox Catalysis
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T13%3A20%3A05IST&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=Synthesis%20of%202,4,6-Trisubstituted%20Pyridines%20by%20Oxidative%20Eosin%20Y%20Photoredox%20Catalysis&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Rohokale,%20Rajendra%20S&rft.date=2016-08-19&rft.volume=81&rft.issue=16&rft.spage=7121&rft.epage=7126&rft.pages=7121-7126&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.6b00979&rft_dat=%3Cproquest_cross%3E1812884130%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a399t-6f5fec778442930564db82a32b7a61dfbf2baa301b24afde9cc6ab41800a1cb23%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1812884130&rft_id=info:pmid/27362746&rfr_iscdi=true