anti-Carbopalladation Cascades of Internal Alkynes Terminated by Intermolecular Suzuki and Sonogashira Reactions
In this report, we describe Pd-catalyzed cascade reactions in which two internal alkynes undergo two trans-carbocarbonation reactions, leading to new carbon–carbon bonds across the emerging double bonds. The resulting vinyl Pd intermediate being obtained after two carbopalladations is involved in ei...
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| Veröffentlicht in: | Organic letters 2024-12, Vol.26 (48), p.10404-10408 |
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| container_title | Organic letters |
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| creator | Kalvani, Pedram Werz, Daniel B. |
| description | In this report, we describe Pd-catalyzed cascade reactions in which two internal alkynes undergo two trans-carbocarbonation reactions, leading to new carbon–carbon bonds across the emerging double bonds. The resulting vinyl Pd intermediate being obtained after two carbopalladations is involved in either terminating Suzuki or Sonogashira reactions leading to either highly substituted butadienes or hexadienynes. A variety of different precursors as well as boronic acids and alkynes, respectively, were employed, yielding a broad spectrum of the corresponding products in yields of up to 82%. |
| doi_str_mv | 10.1021/acs.orglett.4c04114 |
| format | Article |
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The resulting vinyl Pd intermediate being obtained after two carbopalladations is involved in either terminating Suzuki or Sonogashira reactions leading to either highly substituted butadienes or hexadienynes. A variety of different precursors as well as boronic acids and alkynes, respectively, were employed, yielding a broad spectrum of the corresponding products in yields of up to 82%.</description><identifier>ISSN: 1523-7060</identifier><identifier>ISSN: 1523-7052</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.4c04114</identifier><identifier>PMID: 39571182</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>alkynes ; boronic acids ; butadienes ; chemical bonding ; Suzuki reaction</subject><ispartof>Organic letters, 2024-12, Vol.26 (48), p.10404-10408</ispartof><rights>2024 The Authors. 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A variety of different precursors as well as boronic acids and alkynes, respectively, were employed, yielding a broad spectrum of the corresponding products in yields of up to 82%.</description><subject>alkynes</subject><subject>boronic acids</subject><subject>butadienes</subject><subject>chemical bonding</subject><subject>Suzuki reaction</subject><issn>1523-7060</issn><issn>1523-7052</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqNkc1OwzAQhC0EoqXwBEjIRy5p7ThOnGNV8VOpEhIt52jjOCVtYgc7OZSnx1VDj4iTrd1vZrU7CN1TMqUkpDOQbmrstlZdN40kiSiNLtCY8pAFCeHh5fkfkxG6cW5HCPWV9BqNWMoTSkU4Ri3orgoWYHPTQl1DAV1lNF6Ak1Aoh02Jl7pTVkON5_X-oH1to2xTaehUgfPDqd2YWsm-BovX_Xe_rzDoAq-NNltwn5UF_K5AHp3dLboqoXbqbngn6OP5abN4DVZvL8vFfBVAyEUXpHkqmOBckVDyQpY04olULCU0ZVxQlaeMFWUU8jgui4QIEER6Ni_jJBFlQtkEPZ58W2u-euW6rKmcVH5FrUzvMka5V_sJ_0EZFVEak8Sj7IRKa5yzqsxaWzVgDxkl2TGVzKeSDalkQype9TAM6PNGFWfNbwwemJ2Ao3pn-uO53Z-WPy2PnFY</recordid><startdate>20241206</startdate><enddate>20241206</enddate><creator>Kalvani, Pedram</creator><creator>Werz, Daniel B.</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0002-3973-2212</orcidid></search><sort><creationdate>20241206</creationdate><title>anti-Carbopalladation Cascades of Internal Alkynes Terminated by Intermolecular Suzuki and Sonogashira Reactions</title><author>Kalvani, Pedram ; Werz, Daniel B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a258t-9b983855e02c5dcf1457ce390193581eb933df42566fd708a80ce02bf6778f713</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>alkynes</topic><topic>boronic acids</topic><topic>butadienes</topic><topic>chemical bonding</topic><topic>Suzuki reaction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kalvani, Pedram</creatorcontrib><creatorcontrib>Werz, Daniel B.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kalvani, Pedram</au><au>Werz, Daniel B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>anti-Carbopalladation Cascades of Internal Alkynes Terminated by Intermolecular Suzuki and Sonogashira Reactions</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2024-12-06</date><risdate>2024</risdate><volume>26</volume><issue>48</issue><spage>10404</spage><epage>10408</epage><pages>10404-10408</pages><issn>1523-7060</issn><issn>1523-7052</issn><eissn>1523-7052</eissn><abstract>In this report, we describe Pd-catalyzed cascade reactions in which two internal alkynes undergo two trans-carbocarbonation reactions, leading to new carbon–carbon bonds across the emerging double bonds. The resulting vinyl Pd intermediate being obtained after two carbopalladations is involved in either terminating Suzuki or Sonogashira reactions leading to either highly substituted butadienes or hexadienynes. 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| language | eng |
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| source | ACS Publications |
| subjects | alkynes boronic acids butadienes chemical bonding Suzuki reaction |
| title | anti-Carbopalladation Cascades of Internal Alkynes Terminated by Intermolecular Suzuki and Sonogashira Reactions |
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