Microwave-enhanced cross-coupling reactions involving alkynyltrifluoroborates with aryl bromides

Palladium-catalyzed alkynylation has emerged as one of the most reliable methods for the synthesis of alkynes which are often used in natural product syntheses and material science. An efficient method for coupling alkynyltrifluoroborates with various aryl bromides in the presence of a palladium cat...

Full description

Saved in:
Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2013-01, Vol.18 (2), p.1755-1761
Main Authors: Coltuclu, Vitali, Dadush, Eric, Naravane, Abhijit, Kabalka, George W
Format: Article
Language:English
Subjects:
alkynes
BASIC BIOLOGICAL SCIENCES
Borates - chemistry
Bromides - chemistry
Chemistry, Organic - methods
Chromatography
coupling reactions
INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
microwave
Microwaves
Natural products
organotrifluoroborates
Palladium
Potassium
Reagents
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites cdi_FETCH-LOGICAL-c472t-80247549fbbeb6efdad8f35e308caab676666fc416ea34bc66bcff5e836103993
container_end_page 1761
container_issue 2
container_start_page 1755
container_title Molecules (Basel, Switzerland)
container_volume 18
creator Coltuclu, Vitali
Dadush, Eric
Naravane, Abhijit
Kabalka, George W
description Palladium-catalyzed alkynylation has emerged as one of the most reliable methods for the synthesis of alkynes which are often used in natural product syntheses and material science. An efficient method for coupling alkynyltrifluoroborates with various aryl bromides in the presence of a palladium catalyst has been developed using microwave irradiation. The microwave reactions are rapid and efficient.
doi_str_mv 10.3390/molecules18021755
format article
fullrecord <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_23f583f7f551467981b3431141284d6f</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_23f583f7f551467981b3431141284d6f</doaj_id><sourcerecordid>1312657152</sourcerecordid><originalsourceid>FETCH-LOGICAL-c472t-80247549fbbeb6efdad8f35e308caab676666fc416ea34bc66bcff5e836103993</originalsourceid><addsrcrecordid>eNplUstu1DAUjRCIlsIHsEERbNgE_E6yQaoqHpWK2MDa2M71jAePPdjOVPP3OJ1SteCNreNzzz330TQvMXpH6Yjeb6MHM3vIeEAE95w_ak4xI6ijiI2P771Pmmc5b1AlMcyfNieEMsoGgU-bn1-dSfFa7aGDsFbBwNRWIOfOxHnnXVi1CZQpLobcurCPfr9gyv86hIMvyVk_xxR1TKpAbq9dWbcqHXyrU9y6CfLz5olVPsOL2_us-fHp4_eLL93Vt8-XF-dXnWE9KV0tgPWcjVZr0ALspKbBUg4UDUYpLXpRjzUMC1CUaSOENtZyGKjAiI4jPWsuj7pTVBu5S25bbcionLwBYlpJlYozHiShlg_U9pZzzEQ_DljXfuDaGzKwSdiq9eGotZv1FiYDoSTlH4g-_AluLVdxLwXpEeOLmddHgZiLk9m4AmZtYghgisSipulJJb29zZLi7xlykVuXDXivAsQ5S0wxEbzHfKG--Ye6iXMKtZ8Sc0pQHSVasuIj62aACeydY4zksjDyv4WpMa_ul3oX8XdD6B9o28Ai</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1532086109</pqid></control><display><type>article</type><title>Microwave-enhanced cross-coupling reactions involving alkynyltrifluoroborates with aryl bromides</title><source>Publicly Available Content Database</source><source>PubMed Central(OpenAccess)</source><creator>Coltuclu, Vitali ; Dadush, Eric ; Naravane, Abhijit ; Kabalka, George W</creator><creatorcontrib>Coltuclu, Vitali ; Dadush, Eric ; Naravane, Abhijit ; Kabalka, George W ; Univ. of Tennessee, Knoxville, TN (United States)</creatorcontrib><description>Palladium-catalyzed alkynylation has emerged as one of the most reliable methods for the synthesis of alkynes which are often used in natural product syntheses and material science. An efficient method for coupling alkynyltrifluoroborates with various aryl bromides in the presence of a palladium catalyst has been developed using microwave irradiation. The microwave reactions are rapid and efficient.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules18021755</identifier><identifier>PMID: 23434861</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>alkynes ; BASIC BIOLOGICAL SCIENCES ; Borates - chemistry ; Bromides - chemistry ; Chemistry, Organic - methods ; Chromatography ; coupling reactions ; INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY ; microwave ; Microwaves ; Natural products ; organotrifluoroborates ; Palladium ; Potassium ; Reagents</subject><ispartof>Molecules (Basel, Switzerland), 2013-01, Vol.18 (2), p.1755-1761</ispartof><rights>Copyright MDPI AG 2013</rights><rights>2013 by the authors; 2013</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c472t-80247549fbbeb6efdad8f35e308caab676666fc416ea34bc66bcff5e836103993</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/1532086109/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/1532086109?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23434861$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/servlets/purl/1628472$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Coltuclu, Vitali</creatorcontrib><creatorcontrib>Dadush, Eric</creatorcontrib><creatorcontrib>Naravane, Abhijit</creatorcontrib><creatorcontrib>Kabalka, George W</creatorcontrib><creatorcontrib>Univ. of Tennessee, Knoxville, TN (United States)</creatorcontrib><title>Microwave-enhanced cross-coupling reactions involving alkynyltrifluoroborates with aryl bromides</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>Palladium-catalyzed alkynylation has emerged as one of the most reliable methods for the synthesis of alkynes which are often used in natural product syntheses and material science. An efficient method for coupling alkynyltrifluoroborates with various aryl bromides in the presence of a palladium catalyst has been developed using microwave irradiation. The microwave reactions are rapid and efficient.</description><subject>alkynes</subject><subject>BASIC BIOLOGICAL SCIENCES</subject><subject>Borates - chemistry</subject><subject>Bromides - chemistry</subject><subject>Chemistry, Organic - methods</subject><subject>Chromatography</subject><subject>coupling reactions</subject><subject>INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY</subject><subject>microwave</subject><subject>Microwaves</subject><subject>Natural products</subject><subject>organotrifluoroborates</subject><subject>Palladium</subject><subject>Potassium</subject><subject>Reagents</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNplUstu1DAUjRCIlsIHsEERbNgE_E6yQaoqHpWK2MDa2M71jAePPdjOVPP3OJ1SteCNreNzzz330TQvMXpH6Yjeb6MHM3vIeEAE95w_ak4xI6ijiI2P771Pmmc5b1AlMcyfNieEMsoGgU-bn1-dSfFa7aGDsFbBwNRWIOfOxHnnXVi1CZQpLobcurCPfr9gyv86hIMvyVk_xxR1TKpAbq9dWbcqHXyrU9y6CfLz5olVPsOL2_us-fHp4_eLL93Vt8-XF-dXnWE9KV0tgPWcjVZr0ALspKbBUg4UDUYpLXpRjzUMC1CUaSOENtZyGKjAiI4jPWsuj7pTVBu5S25bbcionLwBYlpJlYozHiShlg_U9pZzzEQ_DljXfuDaGzKwSdiq9eGotZv1FiYDoSTlH4g-_AluLVdxLwXpEeOLmddHgZiLk9m4AmZtYghgisSipulJJb29zZLi7xlykVuXDXivAsQ5S0wxEbzHfKG--Ye6iXMKtZ8Sc0pQHSVasuIj62aACeydY4zksjDyv4WpMa_ul3oX8XdD6B9o28Ai</recordid><startdate>20130129</startdate><enddate>20130129</enddate><creator>Coltuclu, Vitali</creator><creator>Dadush, Eric</creator><creator>Naravane, Abhijit</creator><creator>Kabalka, George W</creator><general>MDPI AG</general><general>MDPI</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>OIOZB</scope><scope>OTOTI</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20130129</creationdate><title>Microwave-enhanced cross-coupling reactions involving alkynyltrifluoroborates with aryl bromides</title><author>Coltuclu, Vitali ; Dadush, Eric ; Naravane, Abhijit ; Kabalka, George W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c472t-80247549fbbeb6efdad8f35e308caab676666fc416ea34bc66bcff5e836103993</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>alkynes</topic><topic>BASIC BIOLOGICAL SCIENCES</topic><topic>Borates - chemistry</topic><topic>Bromides - chemistry</topic><topic>Chemistry, Organic - methods</topic><topic>Chromatography</topic><topic>coupling reactions</topic><topic>INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY</topic><topic>microwave</topic><topic>Microwaves</topic><topic>Natural products</topic><topic>organotrifluoroborates</topic><topic>Palladium</topic><topic>Potassium</topic><topic>Reagents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Coltuclu, Vitali</creatorcontrib><creatorcontrib>Dadush, Eric</creatorcontrib><creatorcontrib>Naravane, Abhijit</creatorcontrib><creatorcontrib>Kabalka, George W</creatorcontrib><creatorcontrib>Univ. of Tennessee, Knoxville, TN (United States)</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health &amp; Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health &amp; Medical Complete (Alumni)</collection><collection>Health &amp; Medical Collection (Alumni Edition)</collection><collection>PML(ProQuest Medical Library)</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>OSTI.GOV - Hybrid</collection><collection>OSTI.GOV</collection><collection>PubMed Central (Full Participant titles)</collection><collection>Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Coltuclu, Vitali</au><au>Dadush, Eric</au><au>Naravane, Abhijit</au><au>Kabalka, George W</au><aucorp>Univ. of Tennessee, Knoxville, TN (United States)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave-enhanced cross-coupling reactions involving alkynyltrifluoroborates with aryl bromides</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2013-01-29</date><risdate>2013</risdate><volume>18</volume><issue>2</issue><spage>1755</spage><epage>1761</epage><pages>1755-1761</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>Palladium-catalyzed alkynylation has emerged as one of the most reliable methods for the synthesis of alkynes which are often used in natural product syntheses and material science. An efficient method for coupling alkynyltrifluoroborates with various aryl bromides in the presence of a palladium catalyst has been developed using microwave irradiation. The microwave reactions are rapid and efficient.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>23434861</pmid><doi>10.3390/molecules18021755</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1420-3049
ispartof Molecules (Basel, Switzerland), 2013-01, Vol.18 (2), p.1755-1761
issn 1420-3049
1420-3049
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_23f583f7f551467981b3431141284d6f
source Publicly Available Content Database; PubMed Central(OpenAccess)
subjects alkynes
BASIC BIOLOGICAL SCIENCES
Borates - chemistry
Bromides - chemistry
Chemistry, Organic - methods
Chromatography
coupling reactions
INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
microwave
Microwaves
Natural products
organotrifluoroborates
Palladium
Potassium
Reagents
title Microwave-enhanced cross-coupling reactions involving alkynyltrifluoroborates with aryl bromides
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T19%3A41%3A02IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Microwave-enhanced%20cross-coupling%20reactions%20involving%20alkynyltrifluoroborates%20with%20aryl%20bromides&rft.jtitle=Molecules%20(Basel,%20Switzerland)&rft.au=Coltuclu,%20Vitali&rft.aucorp=Univ.%20of%20Tennessee,%20Knoxville,%20TN%20(United%20States)&rft.date=2013-01-29&rft.volume=18&rft.issue=2&rft.spage=1755&rft.epage=1761&rft.pages=1755-1761&rft.issn=1420-3049&rft.eissn=1420-3049&rft_id=info:doi/10.3390/molecules18021755&rft_dat=%3Cproquest_doaj_%3E1312657152%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c472t-80247549fbbeb6efdad8f35e308caab676666fc416ea34bc66bcff5e836103993%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1532086109&rft_id=info:pmid/23434861&rfr_iscdi=true