Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides
We report a palladium‐catalyzed method to synthesize acid chlorides by the chlorocarbonylation of aryl bromides. Mechanistic studies suggest the combination of sterically encumbered PtBu3 and CO coordination to palladium can rapidly equilibrate the oxidative addition/reductive elimination of carbon–...
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| Veröffentlicht in: | Chemistry : a European journal 2015-06, Vol.21 (26), p.9550-9555 |
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| container_issue | 26 |
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| container_title | Chemistry : a European journal |
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| creator | Quesnel, Jeffrey S. Kayser, Laure V. Fabrikant, Alexander Arndtsen, Bruce A. |
| description | We report a palladium‐catalyzed method to synthesize acid chlorides by the chlorocarbonylation of aryl bromides. Mechanistic studies suggest the combination of sterically encumbered PtBu3 and CO coordination to palladium can rapidly equilibrate the oxidative addition/reductive elimination of carbon–halogen bonds. This provides a useful method to assemble highly reactive acid chlorides from stable and available reagents, and can be coupled with subsequent nucleophilic reactions to generate new classes of carbonylated products.
The Good, the Bad and the Bulky! By employing a sterically encumbered phosphine ligand, tri‐tert‐butyl phosphine, under palladium catalysis inert aryl bromides are chlorocarbonylated to create reactive acid chlorides by reversible carbon–halogen bond reductive elimination. This general platform allows for an expanded scope of the Heck carbonylation reaction to include previously incompatible nucleophiles. |
| doi_str_mv | 10.1002/chem.201500476 |
| format | Article |
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The Good, the Bad and the Bulky! By employing a sterically encumbered phosphine ligand, tri‐tert‐butyl phosphine, under palladium catalysis inert aryl bromides are chlorocarbonylated to create reactive acid chlorides by reversible carbon–halogen bond reductive elimination. This general platform allows for an expanded scope of the Heck carbonylation reaction to include previously incompatible nucleophiles.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201500476</identifier><identifier>PMID: 25982536</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>acid chloride ; Aromatic compounds ; Bromides ; carbonylation ; Carbonyls ; Chemistry ; Chlorides ; Halocarbons ; Inert ; mechanism ; Palladium ; Phosphines ; reductive elimination</subject><ispartof>Chemistry : a European journal, 2015-06, Vol.21 (26), p.9550-9555</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5476-7e4c68e4e11d272396e5a52c6844ef7757737748c2dc9c100ed853897b094c703</citedby><cites>FETCH-LOGICAL-c5476-7e4c68e4e11d272396e5a52c6844ef7757737748c2dc9c100ed853897b094c703</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201500476$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201500476$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25982536$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Quesnel, Jeffrey S.</creatorcontrib><creatorcontrib>Kayser, Laure V.</creatorcontrib><creatorcontrib>Fabrikant, Alexander</creatorcontrib><creatorcontrib>Arndtsen, Bruce A.</creatorcontrib><title>Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>We report a palladium‐catalyzed method to synthesize acid chlorides by the chlorocarbonylation of aryl bromides. Mechanistic studies suggest the combination of sterically encumbered PtBu3 and CO coordination to palladium can rapidly equilibrate the oxidative addition/reductive elimination of carbon–halogen bonds. This provides a useful method to assemble highly reactive acid chlorides from stable and available reagents, and can be coupled with subsequent nucleophilic reactions to generate new classes of carbonylated products.
The Good, the Bad and the Bulky! By employing a sterically encumbered phosphine ligand, tri‐tert‐butyl phosphine, under palladium catalysis inert aryl bromides are chlorocarbonylated to create reactive acid chlorides by reversible carbon–halogen bond reductive elimination. This general platform allows for an expanded scope of the Heck carbonylation reaction to include previously incompatible nucleophiles.</description><subject>acid chloride</subject><subject>Aromatic compounds</subject><subject>Bromides</subject><subject>carbonylation</subject><subject>Carbonyls</subject><subject>Chemistry</subject><subject>Chlorides</subject><subject>Halocarbons</subject><subject>Inert</subject><subject>mechanism</subject><subject>Palladium</subject><subject>Phosphines</subject><subject>reductive elimination</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkUtv1DAUhS1ERYfCliWKxIZNpn47Xk5DH0gtVLy6tDzOHY1LErd2Ipr-ejyaYYS66cqW9Z3je-5B6B3Bc4IxPXZr6OYUE4ExV_IFmhFBScmUFC_RDGuuSimYPkSvU7rFGGvJ2Ct0SIWuqGByhm4WzjdFvW5D9A0U36d-WEPyqVhORb4V17ZtbePHrqztYNvpEXZ0cDYuQz-1dvChL8KqWMSpLU5i6LJReoMOVrZN8HZ3HqGfZ6c_6ovy8uv553pxWTqR5y0VcCcr4EBIQxVlWoKwguY3zmGllFCKKcUrRxunXU4MTSVYpdUyZ3MKsyP0cet7F8P9CGkwnU8O8tA9hDEZoipJ1Oav51GpsRSU043rhyfobRhjn4NkqtKV1kTyTM23lIshpQgrcxd9Z-NkCDabdsymHbNvJwve72zHZQfNHv9XRwb0FvjjW5iesTP1xenV_-blVuvTAA97rY2_jcxLFObmy7k5OfslxDf8yVyzv9cvqJg</recordid><startdate>20150622</startdate><enddate>20150622</enddate><creator>Quesnel, Jeffrey S.</creator><creator>Kayser, Laure V.</creator><creator>Fabrikant, Alexander</creator><creator>Arndtsen, Bruce A.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20150622</creationdate><title>Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides</title><author>Quesnel, Jeffrey S. ; Kayser, Laure V. ; Fabrikant, Alexander ; Arndtsen, Bruce A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5476-7e4c68e4e11d272396e5a52c6844ef7757737748c2dc9c100ed853897b094c703</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>acid chloride</topic><topic>Aromatic compounds</topic><topic>Bromides</topic><topic>carbonylation</topic><topic>Carbonyls</topic><topic>Chemistry</topic><topic>Chlorides</topic><topic>Halocarbons</topic><topic>Inert</topic><topic>mechanism</topic><topic>Palladium</topic><topic>Phosphines</topic><topic>reductive elimination</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Quesnel, Jeffrey S.</creatorcontrib><creatorcontrib>Kayser, Laure V.</creatorcontrib><creatorcontrib>Fabrikant, Alexander</creatorcontrib><creatorcontrib>Arndtsen, Bruce A.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Quesnel, Jeffrey S.</au><au>Kayser, Laure V.</au><au>Fabrikant, Alexander</au><au>Arndtsen, Bruce A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2015-06-22</date><risdate>2015</risdate><volume>21</volume><issue>26</issue><spage>9550</spage><epage>9555</epage><pages>9550-9555</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>We report a palladium‐catalyzed method to synthesize acid chlorides by the chlorocarbonylation of aryl bromides. Mechanistic studies suggest the combination of sterically encumbered PtBu3 and CO coordination to palladium can rapidly equilibrate the oxidative addition/reductive elimination of carbon–halogen bonds. This provides a useful method to assemble highly reactive acid chlorides from stable and available reagents, and can be coupled with subsequent nucleophilic reactions to generate new classes of carbonylated products.
The Good, the Bad and the Bulky! By employing a sterically encumbered phosphine ligand, tri‐tert‐butyl phosphine, under palladium catalysis inert aryl bromides are chlorocarbonylated to create reactive acid chlorides by reversible carbon–halogen bond reductive elimination. This general platform allows for an expanded scope of the Heck carbonylation reaction to include previously incompatible nucleophiles.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25982536</pmid><doi>10.1002/chem.201500476</doi><tpages>6</tpages></addata></record> |
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| language | eng |
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| source | Wiley Online Library |
| subjects | acid chloride Aromatic compounds Bromides carbonylation Carbonyls Chemistry Chlorides Halocarbons Inert mechanism Palladium Phosphines reductive elimination |
| title | Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides |
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