Direct Transformation of Aryl 2‑Pyridyl Esters to Secondary Benzylic Alcohols by Nickel Relay Catalysis

Direct Transformation of Aryl 2‑Pyridyl Esters to Secondary Benzylic Alcohols by Nickel Relay Catalysis

A direct transformation of aryl esters to secondary benzylic alcohols via tandem Ni-catalyzed cross-coupling reactions of aromatic 2-pyridyl esters with alkyl zinc reagents and carbonyl group reduction by Ni–H species is achieved. Preliminary mechanistic studies reveal that the Ni–H species is gener...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2019-04, Vol.21 (7), p.2453-2458
Hauptverfasser: Wu, Xianqing, Li, Xiaobin, Huang, Wenyi, Wang, Yun, Xu, Hui, Cai, Liangzhen, Qu, Jingping, Chen, Yifeng
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 2458
container_issue 7
container_start_page 2453
container_title Organic letters
container_volume 21
creator Wu, Xianqing
Li, Xiaobin
Huang, Wenyi
Wang, Yun
Xu, Hui
Cai, Liangzhen
Qu, Jingping
Chen, Yifeng
description A direct transformation of aryl esters to secondary benzylic alcohols via tandem Ni-catalyzed cross-coupling reactions of aromatic 2-pyridyl esters with alkyl zinc reagents and carbonyl group reduction by Ni–H species is achieved. Preliminary mechanistic studies reveal that the Ni–H species is generated in situ via β-hydride elimination of the Negishi reagents. The reaction is catalyzed by bench-stable nickel salts under mild conditions with wide functional group tolerance.
doi_str_mv 10.1021/acs.orglett.9b00774
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2194153590</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2194153590</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-5f26c882a6137ad62d63d6211740af883ac5bf83262017b4ea55aa8d9940c9393</originalsourceid><addsrcrecordid>eNp9kLlOxDAQhi0E4n4CJOSSJrs-4hzlsiyHhABx1NHEccDgxGA7Rah4BV6RJ8FoF0qamdHo_-f4EDqgZEIJo1OQfmLdo1EhTMqakDxP19A2FYwnORFs_a_OyBba8f6ZEBo75Sba4qQoOE3ZNtIn2ikZ8L2D3rfWdRC07bFt8cyNBrOvj8-b0ekm1gsflPM4WHynpO0bcCM-Vv37aLTEMyPtkzUe1yO-0vJFGXyrDIx4DgHM6LXfQxstGK_2V3kXPZwu7ufnyeX12cV8dpkAT0VIRMsyWRQMMspzaDLWZDxGSvOUQBvPBinqtuAsY4TmdapACICiKcuUyJKXfBcdLee-Ovs2KB-qTnupjIFe2cFXjJYpFVyUJEr5Uiqd9d6ptnp1uot_VZRUP4yryLhaMa5WjKPrcLVgqDvV_Hl-oUbBdCn4cT_bwfXx339HfgOHXYvy</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2194153590</pqid></control><display><type>article</type><title>Direct Transformation of Aryl 2‑Pyridyl Esters to Secondary Benzylic Alcohols by Nickel Relay Catalysis</title><source>ACS Publications</source><creator>Wu, Xianqing ; Li, Xiaobin ; Huang, Wenyi ; Wang, Yun ; Xu, Hui ; Cai, Liangzhen ; Qu, Jingping ; Chen, Yifeng</creator><creatorcontrib>Wu, Xianqing ; Li, Xiaobin ; Huang, Wenyi ; Wang, Yun ; Xu, Hui ; Cai, Liangzhen ; Qu, Jingping ; Chen, Yifeng</creatorcontrib><description>A direct transformation of aryl esters to secondary benzylic alcohols via tandem Ni-catalyzed cross-coupling reactions of aromatic 2-pyridyl esters with alkyl zinc reagents and carbonyl group reduction by Ni–H species is achieved. Preliminary mechanistic studies reveal that the Ni–H species is generated in situ via β-hydride elimination of the Negishi reagents. The reaction is catalyzed by bench-stable nickel salts under mild conditions with wide functional group tolerance.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.9b00774</identifier><identifier>PMID: 30883142</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2019-04, Vol.21 (7), p.2453-2458</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-5f26c882a6137ad62d63d6211740af883ac5bf83262017b4ea55aa8d9940c9393</citedby><cites>FETCH-LOGICAL-a345t-5f26c882a6137ad62d63d6211740af883ac5bf83262017b4ea55aa8d9940c9393</cites><orcidid>0000-0003-3239-6209 ; 0000-0002-7576-0798</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.9b00774$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.9b00774$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30883142$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wu, Xianqing</creatorcontrib><creatorcontrib>Li, Xiaobin</creatorcontrib><creatorcontrib>Huang, Wenyi</creatorcontrib><creatorcontrib>Wang, Yun</creatorcontrib><creatorcontrib>Xu, Hui</creatorcontrib><creatorcontrib>Cai, Liangzhen</creatorcontrib><creatorcontrib>Qu, Jingping</creatorcontrib><creatorcontrib>Chen, Yifeng</creatorcontrib><title>Direct Transformation of Aryl 2‑Pyridyl Esters to Secondary Benzylic Alcohols by Nickel Relay Catalysis</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A direct transformation of aryl esters to secondary benzylic alcohols via tandem Ni-catalyzed cross-coupling reactions of aromatic 2-pyridyl esters with alkyl zinc reagents and carbonyl group reduction by Ni–H species is achieved. Preliminary mechanistic studies reveal that the Ni–H species is generated in situ via β-hydride elimination of the Negishi reagents. The reaction is catalyzed by bench-stable nickel salts under mild conditions with wide functional group tolerance.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kLlOxDAQhi0E4n4CJOSSJrs-4hzlsiyHhABx1NHEccDgxGA7Rah4BV6RJ8FoF0qamdHo_-f4EDqgZEIJo1OQfmLdo1EhTMqakDxP19A2FYwnORFs_a_OyBba8f6ZEBo75Sba4qQoOE3ZNtIn2ikZ8L2D3rfWdRC07bFt8cyNBrOvj8-b0ekm1gsflPM4WHynpO0bcCM-Vv37aLTEMyPtkzUe1yO-0vJFGXyrDIx4DgHM6LXfQxstGK_2V3kXPZwu7ufnyeX12cV8dpkAT0VIRMsyWRQMMspzaDLWZDxGSvOUQBvPBinqtuAsY4TmdapACICiKcuUyJKXfBcdLee-Ovs2KB-qTnupjIFe2cFXjJYpFVyUJEr5Uiqd9d6ptnp1uot_VZRUP4yryLhaMa5WjKPrcLVgqDvV_Hl-oUbBdCn4cT_bwfXx339HfgOHXYvy</recordid><startdate>20190405</startdate><enddate>20190405</enddate><creator>Wu, Xianqing</creator><creator>Li, Xiaobin</creator><creator>Huang, Wenyi</creator><creator>Wang, Yun</creator><creator>Xu, Hui</creator><creator>Cai, Liangzhen</creator><creator>Qu, Jingping</creator><creator>Chen, Yifeng</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-3239-6209</orcidid><orcidid>https://orcid.org/0000-0002-7576-0798</orcidid></search><sort><creationdate>20190405</creationdate><title>Direct Transformation of Aryl 2‑Pyridyl Esters to Secondary Benzylic Alcohols by Nickel Relay Catalysis</title><author>Wu, Xianqing ; Li, Xiaobin ; Huang, Wenyi ; Wang, Yun ; Xu, Hui ; Cai, Liangzhen ; Qu, Jingping ; Chen, Yifeng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-5f26c882a6137ad62d63d6211740af883ac5bf83262017b4ea55aa8d9940c9393</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Xianqing</creatorcontrib><creatorcontrib>Li, Xiaobin</creatorcontrib><creatorcontrib>Huang, Wenyi</creatorcontrib><creatorcontrib>Wang, Yun</creatorcontrib><creatorcontrib>Xu, Hui</creatorcontrib><creatorcontrib>Cai, Liangzhen</creatorcontrib><creatorcontrib>Qu, Jingping</creatorcontrib><creatorcontrib>Chen, Yifeng</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>Wu, Xianqing</au><au>Li, Xiaobin</au><au>Huang, Wenyi</au><au>Wang, Yun</au><au>Xu, Hui</au><au>Cai, Liangzhen</au><au>Qu, Jingping</au><au>Chen, Yifeng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct Transformation of Aryl 2‑Pyridyl Esters to Secondary Benzylic Alcohols by Nickel Relay Catalysis</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2019-04-05</date><risdate>2019</risdate><volume>21</volume><issue>7</issue><spage>2453</spage><epage>2458</epage><pages>2453-2458</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A direct transformation of aryl esters to secondary benzylic alcohols via tandem Ni-catalyzed cross-coupling reactions of aromatic 2-pyridyl esters with alkyl zinc reagents and carbonyl group reduction by Ni–H species is achieved. Preliminary mechanistic studies reveal that the Ni–H species is generated in situ via β-hydride elimination of the Negishi reagents. The reaction is catalyzed by bench-stable nickel salts under mild conditions with wide functional group tolerance.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>30883142</pmid><doi>10.1021/acs.orglett.9b00774</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-3239-6209</orcidid><orcidid>https://orcid.org/0000-0002-7576-0798</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2019-04, Vol.21 (7), p.2453-2458
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2194153590
source ACS Publications
title Direct Transformation of Aryl 2‑Pyridyl Esters to Secondary Benzylic Alcohols by Nickel Relay Catalysis
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-28T19%3A27%3A46IST&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=Direct%20Transformation%20of%20Aryl%202%E2%80%91Pyridyl%20Esters%20to%20Secondary%20Benzylic%20Alcohols%20by%20Nickel%20Relay%20Catalysis&rft.jtitle=Organic%20letters&rft.au=Wu,%20Xianqing&rft.date=2019-04-05&rft.volume=21&rft.issue=7&rft.spage=2453&rft.epage=2458&rft.pages=2453-2458&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.9b00774&rft_dat=%3Cproquest_cross%3E2194153590%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2194153590&rft_id=info:pmid/30883142&rfr_iscdi=true