NiCl2-Catalyzed Hydrophosphinylation

A new nickel-based catalytic system has been developed for phosphorus−carbon bond formation. The addition of alkyl phosphinates to alkynes is catalyzed by nickel chloride in the absence of added ligand. The reaction generally proceeds in high yields, even with internal alkynes, which were poor subst...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2005-05, Vol.70 (10), p.4064-4072
Main Authors: Ribière, Patrice, Bravo-Altamirano, Karla, Antczak, Monika I, Hawkins, Jennifer D, Montchamp, Jean-Luc
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites
container_end_page 4072
container_issue 10
container_start_page 4064
container_title Journal of organic chemistry
container_volume 70
creator Ribière, Patrice
Bravo-Altamirano, Karla
Antczak, Monika I
Hawkins, Jennifer D
Montchamp, Jean-Luc
description A new nickel-based catalytic system has been developed for phosphorus−carbon bond formation. The addition of alkyl phosphinates to alkynes is catalyzed by nickel chloride in the absence of added ligand. The reaction generally proceeds in high yields, even with internal alkynes, which were poor substrates in our previously reported palladium-catalyzed hydrophosphinylation of alkyl phosphinates. The method is useful for the preparation of H-phosphinate esters and their derivatives. The one-pot synthesis of various important organophosphorus compounds is also demonstrated. The reaction can be conducted with microwave heating.
doi_str_mv 10.1021/jo050096l
format article
fullrecord <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_67807376</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67807376</sourcerecordid><originalsourceid>FETCH-LOGICAL-a307t-74d2d7eacabe11ae125ae993eb95d4236ca5ccaad212130c43172b33b10ff1883</originalsourceid><addsrcrecordid>eNpFkcFOwzAMhiMEYmNw4AUQB-BWcJImaY-ogg00ARLjwiVy01TryNrRtBLl6em0sfnigz99lv0Tck7hlgKjd4sKBEAs3QEZUsEgkDGEh2QIwFjAmeQDcuL9AvoSQhyTARWRkhBHQ3L1UiSOBQk26Lpfm11OuqyuVvPKr-ZF2Tlsiqo8JUc5Om_Ptn1EPh4fZskkmL6On5L7aYAcVBOoMGOZsmgwtZSipUygjWNu01hkIePSoDAGMWOUUQ4m5FSxlPOUQp7TKOIjcrPxrurqu7W-0cvCG-sclrZqvZYqAsWV7MGLLdimS5vpVV0sse70_109cL0F0Bt0eY2lKfyeW5tCAT0XbLjCN_ZnN8f6q1_GldCzt3edhPL5U03Gmu29aLxeVG1d9v_QFPQ6B73Lgf8B5r10-g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67807376</pqid></control><display><type>article</type><title>NiCl2-Catalyzed Hydrophosphinylation</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Ribière, Patrice ; Bravo-Altamirano, Karla ; Antczak, Monika I ; Hawkins, Jennifer D ; Montchamp, Jean-Luc</creator><creatorcontrib>Ribière, Patrice ; Bravo-Altamirano, Karla ; Antczak, Monika I ; Hawkins, Jennifer D ; Montchamp, Jean-Luc</creatorcontrib><description>A new nickel-based catalytic system has been developed for phosphorus−carbon bond formation. The addition of alkyl phosphinates to alkynes is catalyzed by nickel chloride in the absence of added ligand. The reaction generally proceeds in high yields, even with internal alkynes, which were poor substrates in our previously reported palladium-catalyzed hydrophosphinylation of alkyl phosphinates. The method is useful for the preparation of H-phosphinate esters and their derivatives. The one-pot synthesis of various important organophosphorus compounds is also demonstrated. The reaction can be conducted with microwave heating.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo050096l</identifier><identifier>PMID: 15876098</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aliphatic compounds ; Chemistry ; Exact sciences and technology ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2005-05, Vol.70 (10), p.4064-4072</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=16780450$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15876098$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ribière, Patrice</creatorcontrib><creatorcontrib>Bravo-Altamirano, Karla</creatorcontrib><creatorcontrib>Antczak, Monika I</creatorcontrib><creatorcontrib>Hawkins, Jennifer D</creatorcontrib><creatorcontrib>Montchamp, Jean-Luc</creatorcontrib><title>NiCl2-Catalyzed Hydrophosphinylation</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A new nickel-based catalytic system has been developed for phosphorus−carbon bond formation. The addition of alkyl phosphinates to alkynes is catalyzed by nickel chloride in the absence of added ligand. The reaction generally proceeds in high yields, even with internal alkynes, which were poor substrates in our previously reported palladium-catalyzed hydrophosphinylation of alkyl phosphinates. The method is useful for the preparation of H-phosphinate esters and their derivatives. The one-pot synthesis of various important organophosphorus compounds is also demonstrated. The reaction can be conducted with microwave heating.</description><subject>Aliphatic compounds</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNpFkcFOwzAMhiMEYmNw4AUQB-BWcJImaY-ogg00ARLjwiVy01TryNrRtBLl6em0sfnigz99lv0Tck7hlgKjd4sKBEAs3QEZUsEgkDGEh2QIwFjAmeQDcuL9AvoSQhyTARWRkhBHQ3L1UiSOBQk26Lpfm11OuqyuVvPKr-ZF2Tlsiqo8JUc5Om_Ptn1EPh4fZskkmL6On5L7aYAcVBOoMGOZsmgwtZSipUygjWNu01hkIePSoDAGMWOUUQ4m5FSxlPOUQp7TKOIjcrPxrurqu7W-0cvCG-sclrZqvZYqAsWV7MGLLdimS5vpVV0sse70_109cL0F0Bt0eY2lKfyeW5tCAT0XbLjCN_ZnN8f6q1_GldCzt3edhPL5U03Gmu29aLxeVG1d9v_QFPQ6B73Lgf8B5r10-g</recordid><startdate>20050513</startdate><enddate>20050513</enddate><creator>Ribière, Patrice</creator><creator>Bravo-Altamirano, Karla</creator><creator>Antczak, Monika I</creator><creator>Hawkins, Jennifer D</creator><creator>Montchamp, Jean-Luc</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20050513</creationdate><title>NiCl2-Catalyzed Hydrophosphinylation</title><author>Ribière, Patrice ; Bravo-Altamirano, Karla ; Antczak, Monika I ; Hawkins, Jennifer D ; Montchamp, Jean-Luc</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a307t-74d2d7eacabe11ae125ae993eb95d4236ca5ccaad212130c43172b33b10ff1883</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Aliphatic compounds</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ribière, Patrice</creatorcontrib><creatorcontrib>Bravo-Altamirano, Karla</creatorcontrib><creatorcontrib>Antczak, Monika I</creatorcontrib><creatorcontrib>Hawkins, Jennifer D</creatorcontrib><creatorcontrib>Montchamp, Jean-Luc</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ribière, Patrice</au><au>Bravo-Altamirano, Karla</au><au>Antczak, Monika I</au><au>Hawkins, Jennifer D</au><au>Montchamp, Jean-Luc</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>NiCl2-Catalyzed Hydrophosphinylation</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-05-13</date><risdate>2005</risdate><volume>70</volume><issue>10</issue><spage>4064</spage><epage>4072</epage><pages>4064-4072</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A new nickel-based catalytic system has been developed for phosphorus−carbon bond formation. The addition of alkyl phosphinates to alkynes is catalyzed by nickel chloride in the absence of added ligand. The reaction generally proceeds in high yields, even with internal alkynes, which were poor substrates in our previously reported palladium-catalyzed hydrophosphinylation of alkyl phosphinates. The method is useful for the preparation of H-phosphinate esters and their derivatives. The one-pot synthesis of various important organophosphorus compounds is also demonstrated. The reaction can be conducted with microwave heating.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15876098</pmid><doi>10.1021/jo050096l</doi><tpages>9</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2005-05, Vol.70 (10), p.4064-4072
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_67807376
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
title NiCl2-Catalyzed Hydrophosphinylation
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T19%3A43%3A02IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=NiCl2-Catalyzed%20Hydrophosphinylation&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Ribi%C3%A8re,%20Patrice&rft.date=2005-05-13&rft.volume=70&rft.issue=10&rft.spage=4064&rft.epage=4072&rft.pages=4064-4072&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo050096l&rft_dat=%3Cproquest_pubme%3E67807376%3C/proquest_pubme%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a307t-74d2d7eacabe11ae125ae993eb95d4236ca5ccaad212130c43172b33b10ff1883%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=67807376&rft_id=info:pmid/15876098&rfr_iscdi=true