Regio- and Stereoselective Hydrophosphination Reactions of Alkynes with Phosphine−Boranes: Access to Stereodefined Vinylphosphine Derivatives

Vinylphosphine−borane complexes are easily synthesized by regio- and stereoselective hydrophosphination of terminal alkynes with use of secondary phosphine−boranes as hydrophosphinating agent. The regioselectivity of the reaction is efficiently controlled by the choice of the activation process: th...

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Veröffentlicht in:	Journal of organic chemistry 2003-09, Vol.68 (18), p.7016-7022
Hauptverfasser:	Mimeau, David, Gaumont, Annie-Claude
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Organic chemistry Organometalloidal and organometallic compounds P derivatives Preparations and properties
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container_title	Journal of organic chemistry
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creator	Mimeau, David Gaumont, Annie-Claude
description	Vinylphosphine−borane complexes are easily synthesized by regio- and stereoselective hydrophosphination of terminal alkynes with use of secondary phosphine−boranes as hydrophosphinating agent. The regioselectivity of the reaction is efficiently controlled by the choice of the activation process: thermal or metal catalyst activation. The vinylphosphine derivatives are purified by chromatography on silica gel. Scalability of the process is demonstrated on a gram scale. This simple route should promote the use of vinylphosphines as building blocks for organic and organometallic chemistry.
doi_str_mv	10.1021/jo030096q
format	Article
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Org. Chem</addtitle><description>Vinylphosphine−borane complexes are easily synthesized by regio- and stereoselective hydrophosphination of terminal alkynes with use of secondary phosphine−boranes as hydrophosphinating agent. The regioselectivity of the reaction is efficiently controlled by the choice of the activation process: thermal or metal catalyst activation. The vinylphosphine derivatives are purified by chromatography on silica gel. Scalability of the process is demonstrated on a gram scale. This simple route should promote the use of vinylphosphines as building blocks for organic and organometallic chemistry.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Organometalloidal and organometallic compounds</subject><subject>P derivatives</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><recordid>eNptkU1vEzEQhi0EoqFw4A8gX0DisOCP9X5wC-WjoAKhLb1aXu-YuN2sU8-mkBtHuPYn9pfgKEtzYS4eeR698-odQh5z9oIzwV-eByYZq4vLO2TClWBZUbP8LpkwJkQmRSH3yAPEc5ZKKXWf7HFR5wXP5YRcH8N3HzJq-paeDBAhIHRgB38F9HDdxrCcB1zOfW8GH3p6DMZuGqTB0Wl3se4B6Q8_zOls5ODm9_XrEE0avLr59YdOrQVEOoRRvgWXoJae-X7d_RMH-gaivzKbtfiQ3HOmQ3g0vvvk27u3pweH2dGX9x8OpkeZkWU9ZA1UdV5bUNJIJXjBa-eMk9CWglunVGmdyyVzpqnSp6igqXLbVHVlWma5sHKfPNvqLmO4XAEOeuHRQtcl72GFupQFk1JVCXy-BW0MiBGcXka_MHGtOdObA-jbAyT2ySi6ahbQ7sgx8QQ8HQGD1nQuJWU97jjFOctrkbhsy3kc4Oft3MQLXZSyVPp0dqLL2VlZffr8VX_c6RqLyc8q9im7_xj8C0hPruU</recordid><startdate>20030905</startdate><enddate>20030905</enddate><creator>Mimeau, David</creator><creator>Gaumont, Annie-Claude</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20030905</creationdate><title>Regio- and Stereoselective Hydrophosphination Reactions of Alkynes with Phosphine−Boranes: Access to Stereodefined Vinylphosphine Derivatives</title><author>Mimeau, David ; Gaumont, Annie-Claude</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-be8949ce53a3521619ffaf3ed721cf557cff430fab83ed28eb84cb898ad0c12c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Organometalloidal and organometallic compounds</topic><topic>P derivatives</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mimeau, David</creatorcontrib><creatorcontrib>Gaumont, Annie-Claude</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><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>Mimeau, David</au><au>Gaumont, Annie-Claude</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regio- and Stereoselective Hydrophosphination Reactions of Alkynes with Phosphine−Boranes: Access to Stereodefined Vinylphosphine Derivatives</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2003-09-05</date><risdate>2003</risdate><volume>68</volume><issue>18</issue><spage>7016</spage><epage>7022</epage><pages>7016-7022</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Vinylphosphine−borane complexes are easily synthesized by regio- and stereoselective hydrophosphination of terminal alkynes with use of secondary phosphine−boranes as hydrophosphinating agent. The regioselectivity of the reaction is efficiently controlled by the choice of the activation process: thermal or metal catalyst activation. The vinylphosphine derivatives are purified by chromatography on silica gel. Scalability of the process is demonstrated on a gram scale. This simple route should promote the use of vinylphosphines as building blocks for organic and organometallic chemistry.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12946143</pmid><doi>10.1021/jo030096q</doi><tpages>7</tpages></addata></record>
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subjects	Chemistry Exact sciences and technology Organic chemistry Organometalloidal and organometallic compounds P derivatives Preparations and properties
title	Regio- and Stereoselective Hydrophosphination Reactions of Alkynes with Phosphine−Boranes: Access to Stereodefined Vinylphosphine Derivatives
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