HBF4-Catalysed Nucleophilic Substitutions of Propargylic Alcohols
The activity of HBF4 (aqueous solution) as a catalyst in propargylation reactions is presented. Diverse types of nucleophiles were employed in order to form new C–O, C–N and C–C bonds in technical acetone and in air. Good to excellent yields and good chemoselectivities were obtained using low acid l...
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| Veröffentlicht in: | European journal of organic chemistry 2015-12, Vol.2015 (34), p.7544-7549 |
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| container_issue | 34 |
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| container_title | European journal of organic chemistry |
| container_volume | 2015 |
| creator | Barreiro, Elena Sanz-Vidal, Alvaro Tan, Eric Lau, Shing-Hing Sheppard, Tom D. Díez-González, Silvia |
| description | The activity of HBF4 (aqueous solution) as a catalyst in propargylation reactions is presented. Diverse types of nucleophiles were employed in order to form new C–O, C–N and C–C bonds in technical acetone and in air. Good to excellent yields and good chemoselectivities were obtained using low acid loading (typically 1 mol‐%) under simple reaction conditions.
The activity of HBF4 (aq. solution) as a catalyst in propargylation reactions is presented. C–O, C–N and C–C bonds were formed in technical acetone and in air. Good to excellent yields were obtained using low acid loading (typically 1 mol‐%) under mild reaction conditions. |
| doi_str_mv | 10.1002/ejoc.201501249 |
| format | Article |
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The activity of HBF4 (aq. solution) as a catalyst in propargylation reactions is presented. C–O, C–N and C–C bonds were formed in technical acetone and in air. Good to excellent yields were obtained using low acid loading (typically 1 mol‐%) under mild reaction conditions.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201501249</identifier><identifier>PMID: 26693210</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Aqueous solutions ; Brønsted acid ; Friedel-Crafts reaction ; Homogeneous catalysis ; Nucleophilic substitution ; Propargylic alcohols</subject><ispartof>European journal of organic chemistry, 2015-12, Vol.2015 (34), p.7544-7549</ispartof><rights>2015 The Authors. Published by WILEY‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non‐Commercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.</rights><rights>2015 The Authors. Published by WILEY-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.</rights><rights>2015 The Authors. Published by WILEY-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. 2015</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201501249$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201501249$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,780,784,885,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Barreiro, Elena</creatorcontrib><creatorcontrib>Sanz-Vidal, Alvaro</creatorcontrib><creatorcontrib>Tan, Eric</creatorcontrib><creatorcontrib>Lau, Shing-Hing</creatorcontrib><creatorcontrib>Sheppard, Tom D.</creatorcontrib><creatorcontrib>Díez-González, Silvia</creatorcontrib><title>HBF4-Catalysed Nucleophilic Substitutions of Propargylic Alcohols</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>The activity of HBF4 (aqueous solution) as a catalyst in propargylation reactions is presented. Diverse types of nucleophiles were employed in order to form new C–O, C–N and C–C bonds in technical acetone and in air. Good to excellent yields and good chemoselectivities were obtained using low acid loading (typically 1 mol‐%) under simple reaction conditions.
The activity of HBF4 (aq. solution) as a catalyst in propargylation reactions is presented. C–O, C–N and C–C bonds were formed in technical acetone and in air. Good to excellent yields were obtained using low acid loading (typically 1 mol‐%) under mild reaction conditions.</description><subject>Aqueous solutions</subject><subject>Brønsted acid</subject><subject>Friedel-Crafts reaction</subject><subject>Homogeneous catalysis</subject><subject>Nucleophilic substitution</subject><subject>Propargylic alcohols</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNpdUU1PGzEQtapW5avXniP10svCjNdrx5dKYRUICEERqdqb5bW9xKmzDutdIP-ejYIitaeZ0bz39GYeIV8RThGAnrllNKcUsACkTH4ghwhSZsAlfBx6lrMMZf7ngByltAQAyTl-JgeUc5lThEMymZ1fsKzUnQ6b5OzotjfBxfXCB29GD32VOt_1nY9NGsV69LONa90-brbLSTBxEUM6IZ9qHZL78l6Pya-L6bycZTd3l1fl5CbzjA-WqNWUGmuKcV47CdaKiqN0FIvKFpLWJmdSokGwrAbBZEXHnAK1TI75cJLOj8mPne66r1bOGtd0rQ5q3fqVbjcqaq_-3TR-oR7js2JccCrpIPD9XaCNT71LnVr5ZFwIunGxTwrHw1sYZ1QM0G__QZexb5vhPIWiEBQAxRYld6gXH9xm7wRBbaNR22jUPho1vb4r99PAzXZcnzr3uufq9q_iIheF-n17qc7F_L7AWanm-RtFxJHg</recordid><startdate>201512</startdate><enddate>201512</enddate><creator>Barreiro, Elena</creator><creator>Sanz-Vidal, Alvaro</creator><creator>Tan, Eric</creator><creator>Lau, Shing-Hing</creator><creator>Sheppard, Tom D.</creator><creator>Díez-González, Silvia</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>24P</scope><scope>WIN</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>201512</creationdate><title>HBF4-Catalysed Nucleophilic Substitutions of Propargylic Alcohols</title><author>Barreiro, Elena ; Sanz-Vidal, Alvaro ; Tan, Eric ; Lau, Shing-Hing ; Sheppard, Tom D. ; Díez-González, Silvia</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i4699-2da22cdc583fe90dd7b619e215bd592fc34991c10d4f0749b286202d4986099a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Aqueous solutions</topic><topic>Brønsted acid</topic><topic>Friedel-Crafts reaction</topic><topic>Homogeneous catalysis</topic><topic>Nucleophilic substitution</topic><topic>Propargylic alcohols</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Barreiro, Elena</creatorcontrib><creatorcontrib>Sanz-Vidal, Alvaro</creatorcontrib><creatorcontrib>Tan, Eric</creatorcontrib><creatorcontrib>Lau, Shing-Hing</creatorcontrib><creatorcontrib>Sheppard, Tom D.</creatorcontrib><creatorcontrib>Díez-González, Silvia</creatorcontrib><collection>Istex</collection><collection>Wiley-Blackwell Open Access Titles</collection><collection>Wiley Free Content</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Barreiro, Elena</au><au>Sanz-Vidal, Alvaro</au><au>Tan, Eric</au><au>Lau, Shing-Hing</au><au>Sheppard, Tom D.</au><au>Díez-González, Silvia</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>HBF4-Catalysed Nucleophilic Substitutions of Propargylic Alcohols</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2015-12</date><risdate>2015</risdate><volume>2015</volume><issue>34</issue><spage>7544</spage><epage>7549</epage><pages>7544-7549</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The activity of HBF4 (aqueous solution) as a catalyst in propargylation reactions is presented. Diverse types of nucleophiles were employed in order to form new C–O, C–N and C–C bonds in technical acetone and in air. Good to excellent yields and good chemoselectivities were obtained using low acid loading (typically 1 mol‐%) under simple reaction conditions.
The activity of HBF4 (aq. solution) as a catalyst in propargylation reactions is presented. C–O, C–N and C–C bonds were formed in technical acetone and in air. Good to excellent yields were obtained using low acid loading (typically 1 mol‐%) under mild reaction conditions.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26693210</pmid><doi>10.1002/ejoc.201501249</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | European journal of organic chemistry, 2015-12, Vol.2015 (34), p.7544-7549 |
| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aqueous solutions Brønsted acid Friedel-Crafts reaction Homogeneous catalysis Nucleophilic substitution Propargylic alcohols |
| title | HBF4-Catalysed Nucleophilic Substitutions of Propargylic Alcohols |
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