Selective Phosphoranation of Unactivated Alkynes with Phosphonium Cation To Achieve Isoquinoline Synthesis

We herein develop a selective phosphoranation of alkynes with phosphonium cation, which directs a concise approach to isoquinolines from unactivated alkyne and nitrile feedstocks in a single step. Mechanistic studies suggest that the annulation reaction is initiated by the unprecedented phosphoranat...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2021-05, Vol.23 (10), p.4023-4028
Main Authors: Cui, Hong, Bai, Jinku, Ai, Tianyu, Zhan, Ye, Li, Guanzhong, Rao, Honghua
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-c305t-fb9445356c62f62eb4c63a01db34b89a1492f34949d0465d252eac083c7383093
cites cdi_FETCH-LOGICAL-c305t-fb9445356c62f62eb4c63a01db34b89a1492f34949d0465d252eac083c7383093
container_end_page 4028
container_issue 10
container_start_page 4023
container_title Organic letters
container_volume 23
creator Cui, Hong
Bai, Jinku
Ai, Tianyu
Zhan, Ye
Li, Guanzhong
Rao, Honghua
description We herein develop a selective phosphoranation of alkynes with phosphonium cation, which directs a concise approach to isoquinolines from unactivated alkyne and nitrile feedstocks in a single step. Mechanistic studies suggest that the annulation reaction is initiated by the unprecedented phosphoranation of alkynes, thus representing a unique reaction pattern of phosphonium salts and distinguishing it from existing protocols that largely rely on the utilization of highly functionalized imines/oximes and/or highly polarized alkynes.
doi_str_mv 10.1021/acs.orglett.1c01237
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2524360737</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2524360737</sourcerecordid><originalsourceid>FETCH-LOGICAL-c305t-fb9445356c62f62eb4c63a01db34b89a1492f34949d0465d252eac083c7383093</originalsourceid><addsrcrecordid>eNo9kMtOwzAQRS0EolD4AiSUJZsW2-Mk9bKqeFSqBFLbdeQ4E-KS2CV2QP17UvWxmtHMvfM4hDwwOmaUs2el_di1XzWGMGaaMg7pBblhMYdRSmN-ec4TOiC33m8oZX1FXpMBgExoKuGGbJZYow7mF6PPyvlt5VplVTDORq6M1lbteypgEU3r751FH_2ZUJ201nRNNDvIVy6a6spgP2nu3U9nrKuNxWi5s6FCb_wduSpV7fH-GIdk_fqymr2PFh9v89l0MdJA4zAqcylEDHGiE14mHHOhE1CUFTmIfCIVE5KXIKSQBRVJXPCYo9J0AjqFCVAJQ_J0mLtt-zPQh6wxXmNdK4uu81lvENC_D2kvhYNUt877Fsts25pGtbuM0WwPOeshZ0fI2RFy73o8LujyBouz50QV_gGHHnya</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2524360737</pqid></control><display><type>article</type><title>Selective Phosphoranation of Unactivated Alkynes with Phosphonium Cation To Achieve Isoquinoline Synthesis</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Cui, Hong ; Bai, Jinku ; Ai, Tianyu ; Zhan, Ye ; Li, Guanzhong ; Rao, Honghua</creator><creatorcontrib>Cui, Hong ; Bai, Jinku ; Ai, Tianyu ; Zhan, Ye ; Li, Guanzhong ; Rao, Honghua</creatorcontrib><description>We herein develop a selective phosphoranation of alkynes with phosphonium cation, which directs a concise approach to isoquinolines from unactivated alkyne and nitrile feedstocks in a single step. Mechanistic studies suggest that the annulation reaction is initiated by the unprecedented phosphoranation of alkynes, thus representing a unique reaction pattern of phosphonium salts and distinguishing it from existing protocols that largely rely on the utilization of highly functionalized imines/oximes and/or highly polarized alkynes.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.1c01237</identifier><identifier>PMID: 33960793</identifier><language>eng</language><publisher>United States</publisher><ispartof>Organic letters, 2021-05, Vol.23 (10), p.4023-4028</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c305t-fb9445356c62f62eb4c63a01db34b89a1492f34949d0465d252eac083c7383093</citedby><cites>FETCH-LOGICAL-c305t-fb9445356c62f62eb4c63a01db34b89a1492f34949d0465d252eac083c7383093</cites><orcidid>0000-0003-1609-5692</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33960793$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Cui, Hong</creatorcontrib><creatorcontrib>Bai, Jinku</creatorcontrib><creatorcontrib>Ai, Tianyu</creatorcontrib><creatorcontrib>Zhan, Ye</creatorcontrib><creatorcontrib>Li, Guanzhong</creatorcontrib><creatorcontrib>Rao, Honghua</creatorcontrib><title>Selective Phosphoranation of Unactivated Alkynes with Phosphonium Cation To Achieve Isoquinoline Synthesis</title><title>Organic letters</title><addtitle>Org Lett</addtitle><description>We herein develop a selective phosphoranation of alkynes with phosphonium cation, which directs a concise approach to isoquinolines from unactivated alkyne and nitrile feedstocks in a single step. Mechanistic studies suggest that the annulation reaction is initiated by the unprecedented phosphoranation of alkynes, thus representing a unique reaction pattern of phosphonium salts and distinguishing it from existing protocols that largely rely on the utilization of highly functionalized imines/oximes and/or highly polarized alkynes.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNo9kMtOwzAQRS0EolD4AiSUJZsW2-Mk9bKqeFSqBFLbdeQ4E-KS2CV2QP17UvWxmtHMvfM4hDwwOmaUs2el_di1XzWGMGaaMg7pBblhMYdRSmN-ec4TOiC33m8oZX1FXpMBgExoKuGGbJZYow7mF6PPyvlt5VplVTDORq6M1lbteypgEU3r751FH_2ZUJ201nRNNDvIVy6a6spgP2nu3U9nrKuNxWi5s6FCb_wduSpV7fH-GIdk_fqymr2PFh9v89l0MdJA4zAqcylEDHGiE14mHHOhE1CUFTmIfCIVE5KXIKSQBRVJXPCYo9J0AjqFCVAJQ_J0mLtt-zPQh6wxXmNdK4uu81lvENC_D2kvhYNUt877Fsts25pGtbuM0WwPOeshZ0fI2RFy73o8LujyBouz50QV_gGHHnya</recordid><startdate>20210521</startdate><enddate>20210521</enddate><creator>Cui, Hong</creator><creator>Bai, Jinku</creator><creator>Ai, Tianyu</creator><creator>Zhan, Ye</creator><creator>Li, Guanzhong</creator><creator>Rao, Honghua</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1609-5692</orcidid></search><sort><creationdate>20210521</creationdate><title>Selective Phosphoranation of Unactivated Alkynes with Phosphonium Cation To Achieve Isoquinoline Synthesis</title><author>Cui, Hong ; Bai, Jinku ; Ai, Tianyu ; Zhan, Ye ; Li, Guanzhong ; Rao, Honghua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c305t-fb9445356c62f62eb4c63a01db34b89a1492f34949d0465d252eac083c7383093</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cui, Hong</creatorcontrib><creatorcontrib>Bai, Jinku</creatorcontrib><creatorcontrib>Ai, Tianyu</creatorcontrib><creatorcontrib>Zhan, Ye</creatorcontrib><creatorcontrib>Li, Guanzhong</creatorcontrib><creatorcontrib>Rao, Honghua</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>Cui, Hong</au><au>Bai, Jinku</au><au>Ai, Tianyu</au><au>Zhan, Ye</au><au>Li, Guanzhong</au><au>Rao, Honghua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective Phosphoranation of Unactivated Alkynes with Phosphonium Cation To Achieve Isoquinoline Synthesis</atitle><jtitle>Organic letters</jtitle><addtitle>Org Lett</addtitle><date>2021-05-21</date><risdate>2021</risdate><volume>23</volume><issue>10</issue><spage>4023</spage><epage>4028</epage><pages>4023-4028</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>We herein develop a selective phosphoranation of alkynes with phosphonium cation, which directs a concise approach to isoquinolines from unactivated alkyne and nitrile feedstocks in a single step. Mechanistic studies suggest that the annulation reaction is initiated by the unprecedented phosphoranation of alkynes, thus representing a unique reaction pattern of phosphonium salts and distinguishing it from existing protocols that largely rely on the utilization of highly functionalized imines/oximes and/or highly polarized alkynes.</abstract><cop>United States</cop><pmid>33960793</pmid><doi>10.1021/acs.orglett.1c01237</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-1609-5692</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2021-05, Vol.23 (10), p.4023-4028
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2524360737
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Selective Phosphoranation of Unactivated Alkynes with Phosphonium Cation To Achieve Isoquinoline Synthesis
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-09T19%3A29%3A37IST&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=Selective%20Phosphoranation%20of%20Unactivated%20Alkynes%20with%20Phosphonium%20Cation%20To%20Achieve%20Isoquinoline%20Synthesis&rft.jtitle=Organic%20letters&rft.au=Cui,%20Hong&rft.date=2021-05-21&rft.volume=23&rft.issue=10&rft.spage=4023&rft.epage=4028&rft.pages=4023-4028&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.1c01237&rft_dat=%3Cproquest_cross%3E2524360737%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c305t-fb9445356c62f62eb4c63a01db34b89a1492f34949d0465d252eac083c7383093%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2524360737&rft_id=info:pmid/33960793&rfr_iscdi=true