Regioselective Iron‐Catalysed Cross‐Coupling Reaction of Aryl Propargylic Bromides and Aryl Grignard Reagents
An iron‐catalysed Kumada‐type cross‐coupling reaction between aryl substituted propargylic bromides and arylmagnesium reagents has been developed. Propargylic coupling products were the main or only outcome, and propargyl/allene regioselectivity was shown to depend on the electronic nature of the su...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2020-01, Vol.362 (1), p.146-151 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Manjon-Mata, Ines Quiros, M. Teresa Bunuel, Elena Cardenas, Diego J. |
| description | An iron‐catalysed Kumada‐type cross‐coupling reaction between aryl substituted propargylic bromides and arylmagnesium reagents has been developed. Propargylic coupling products were the main or only outcome, and propargyl/allene regioselectivity was shown to depend on the electronic nature of the substituents on the triple bond of the substrate and on the arylmagnesium halide. Best selectivities were observed when electron donating substituents were present in either reagent. The process is stereoespecific, occurs with configuration inversion and no carbon‐based radicals seem to be involved in the mechanism. |
| doi_str_mv | 10.1002/adsc.201901203 |
| format | Article |
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Teresa ; Bunuel, Elena ; Cardenas, Diego J.</creator><creatorcontrib>Manjon-Mata, Ines ; Quiros, M. Teresa ; Bunuel, Elena ; Cardenas, Diego J.</creatorcontrib><description>An iron‐catalysed Kumada‐type cross‐coupling reaction between aryl substituted propargylic bromides and arylmagnesium reagents has been developed. Propargylic coupling products were the main or only outcome, and propargyl/allene regioselectivity was shown to depend on the electronic nature of the substituents on the triple bond of the substrate and on the arylmagnesium halide. Best selectivities were observed when electron donating substituents were present in either reagent. 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The process is stereoespecific, occurs with configuration inversion and no carbon‐based radicals seem to be involved in the mechanism.</description><subject>Allene</subject><subject>Aromatic compounds</subject><subject>Bromides</subject><subject>Chemistry</subject><subject>Chemistry, Applied</subject><subject>Chemistry, Organic</subject><subject>Cross coupling</subject><subject>Grignard reagents</subject><subject>homogeneous catalysis</subject><subject>Iron</subject><subject>Physical Sciences</subject><subject>propargylic bromides</subject><subject>Reagents</subject><subject>Regioselectivity</subject><subject>Science & Technology</subject><subject>Substrates</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>AOWDO</sourceid><recordid>eNqNkMtOxCAUhhujidet6yYuzYwHCp12OdZrYqLxsm4oHBpMhRE6mu58BJ_RJ5FmzLjUFSfwf_DzJckhgSkBoCdCBTmlQEogFLKNZIfkhE8YycvN9cxhO9kN4RmAzIrZbCd5vcfWuIAdyt68YXrtnf36-KxEL7ohoEor70IYd9xy0RnbpvcoYtTZ1Ol07ocuvfNuIXw7dEamp969GIUhFVatTi-9aa3wauRatH3YT7a06AIe_Kx7ydPF-WN1Nbm5vbyu5jcTmXGWTUoqeSxdUNoU0KDKSS6g5ExrxRrNNeNCzzAXglOikChFgUtoFDApCyGLbC85Wt278O51iaGvn93S2_hkTbOM5TxnADE1XaXk-E-Pul548yL8UBOoR631qLVea41AsQLesXE6SINW4hoCAFYWjJI8TkAq04vRVZRn-4ge_x-N6fInbToc_qhVz88eqt-S35MAoBs</recordid><startdate>20200107</startdate><enddate>20200107</enddate><creator>Manjon-Mata, Ines</creator><creator>Quiros, M. 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Teresa</creatorcontrib><creatorcontrib>Bunuel, Elena</creatorcontrib><creatorcontrib>Cardenas, Diego J.</creatorcontrib><collection>Index Chemicus</collection><collection>Web of Science - Science Citation Index Expanded - 2020</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Manjon-Mata, Ines</au><au>Quiros, M. Teresa</au><au>Bunuel, Elena</au><au>Cardenas, Diego J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regioselective Iron‐Catalysed Cross‐Coupling Reaction of Aryl Propargylic Bromides and Aryl Grignard Reagents</atitle><jtitle>Advanced synthesis & catalysis</jtitle><stitle>ADV SYNTH CATAL</stitle><date>2020-01-07</date><risdate>2020</risdate><volume>362</volume><issue>1</issue><spage>146</spage><epage>151</epage><pages>146-151</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>An iron‐catalysed Kumada‐type cross‐coupling reaction between aryl substituted propargylic bromides and arylmagnesium reagents has been developed. Propargylic coupling products were the main or only outcome, and propargyl/allene regioselectivity was shown to depend on the electronic nature of the substituents on the triple bond of the substrate and on the arylmagnesium halide. Best selectivities were observed when electron donating substituents were present in either reagent. The process is stereoespecific, occurs with configuration inversion and no carbon‐based radicals seem to be involved in the mechanism.</abstract><cop>WEINHEIM</cop><pub>Wiley</pub><doi>10.1002/adsc.201901203</doi><tpages>6</tpages></addata></record> |
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| subjects | Allene Aromatic compounds Bromides Chemistry Chemistry, Applied Chemistry, Organic Cross coupling Grignard reagents homogeneous catalysis Iron Physical Sciences propargylic bromides Reagents Regioselectivity Science & Technology Substrates |
| title | Regioselective Iron‐Catalysed Cross‐Coupling Reaction of Aryl Propargylic Bromides and Aryl Grignard Reagents |
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