Regiodivergent Synthesis of 1,3‐ and 1,4‐Enynes through Kinetically Favored Hydropalladation and Ligand‐Enforced Carbopalladation
Pd‐catalyzed hydroalkynylations were developed that involve ligand‐enabled regiodivergent addition of an alkyne to an allenamide, giving branched and linear products stereoselectively and facilitated by the neighboring amide group. Regioselectivity was achieved with the use of (o‐OMePh)3P and BrettP...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2018-07, Vol.57 (31), p.9930-9935 |
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| creator | Pradhan, Tapas R. Kim, Hong Won Park, Jin Kyoon |
| description | Pd‐catalyzed hydroalkynylations were developed that involve ligand‐enabled regiodivergent addition of an alkyne to an allenamide, giving branched and linear products stereoselectively and facilitated by the neighboring amide group. Regioselectivity was achieved with the use of (o‐OMePh)3P and BrettPhos, which allowed the functionalization of various alkynes, including steroids, carbohydrates, alkaloids, chiral ligands, and vitamins. Based on the experimental results, it was proposed that hydro‐ and carbopalladation processes operated during the formations of the branched and linear products, respectively.
Pd‐catalyzed hydroalkynylations involving ligand‐enabled regiodivergent addition of an alkyne to an allenamide stereoselectively gave branched and linear products facilitated by the neighboring amide group. Regioselectivity was achieved with the use of (o‐OMePh)3P and BrettPhos. Hydro‐ and carbopalladation processes were shown to operate during the formation of the branched and linear products, respectively. |
| doi_str_mv | 10.1002/anie.201805408 |
| format | Article |
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Pd‐catalyzed hydroalkynylations involving ligand‐enabled regiodivergent addition of an alkyne to an allenamide stereoselectively gave branched and linear products facilitated by the neighboring amide group. Regioselectivity was achieved with the use of (o‐OMePh)3P and BrettPhos. Hydro‐ and carbopalladation processes were shown to operate during the formation of the branched and linear products, respectively.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201805408</identifier><identifier>PMID: 29985561</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Alkaloids ; Alkynes ; Carbohydrates ; carbopalladation ; diastereoselectivity ; divergent ; hydropalladation ; Ligands ; Regioselectivity ; Steroid hormones ; Steroids ; Vitamins</subject><ispartof>Angewandte Chemie International Edition, 2018-07, Vol.57 (31), p.9930-9935</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5468-d9c873fa7c392cf707f5f8b2a4c21d9dde5232deba2ebfa396eb424c60cd2f9c3</citedby><cites>FETCH-LOGICAL-c5468-d9c873fa7c392cf707f5f8b2a4c21d9dde5232deba2ebfa396eb424c60cd2f9c3</cites><orcidid>0000-0001-6768-2788</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201805408$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201805408$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29985561$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pradhan, Tapas R.</creatorcontrib><creatorcontrib>Kim, Hong Won</creatorcontrib><creatorcontrib>Park, Jin Kyoon</creatorcontrib><title>Regiodivergent Synthesis of 1,3‐ and 1,4‐Enynes through Kinetically Favored Hydropalladation and Ligand‐Enforced Carbopalladation</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Pd‐catalyzed hydroalkynylations were developed that involve ligand‐enabled regiodivergent addition of an alkyne to an allenamide, giving branched and linear products stereoselectively and facilitated by the neighboring amide group. Regioselectivity was achieved with the use of (o‐OMePh)3P and BrettPhos, which allowed the functionalization of various alkynes, including steroids, carbohydrates, alkaloids, chiral ligands, and vitamins. Based on the experimental results, it was proposed that hydro‐ and carbopalladation processes operated during the formations of the branched and linear products, respectively.
Pd‐catalyzed hydroalkynylations involving ligand‐enabled regiodivergent addition of an alkyne to an allenamide stereoselectively gave branched and linear products facilitated by the neighboring amide group. Regioselectivity was achieved with the use of (o‐OMePh)3P and BrettPhos. Hydro‐ and carbopalladation processes were shown to operate during the formation of the branched and linear products, respectively.</description><subject>Alkaloids</subject><subject>Alkynes</subject><subject>Carbohydrates</subject><subject>carbopalladation</subject><subject>diastereoselectivity</subject><subject>divergent</subject><subject>hydropalladation</subject><subject>Ligands</subject><subject>Regioselectivity</subject><subject>Steroid hormones</subject><subject>Steroids</subject><subject>Vitamins</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkT1vFDEQhi1EREJCS4lWoknBHv5Yr-0yOl1IxClIEOqV1x7fObqzD3s3aDs6Wn4jvwQnFwKioZpXo2cejfQi9JLgGcGYvtXBw4xiIjFvsHyCjginpGZCsKclN4zVQnJyiJ7nfFN4KXH7DB1SpSTnLTlC3z_CykfrbyGtIAzVpykMa8g-V9FV5A37-e1HpYMtsSlxEaYAuRrWKY6rdfXeBxi80ZvNVJ3r25jAVheTTXFXVtrqwcdwf730qzLuBS4mU7C5Tv3f2Ak6cHqT4cXDPEafzxfX84t6-eHd5fxsWRvetLK2ykjBnBaGKWqcwMJxJ3uqG0OJVdYCp4xa6DWF3mmmWugb2pgWG0udMuwYne69uxS_jJCHbuuzgfJHgDjmjuJWECYpFwV9_Q96E8cUyneFEkw1BEteqNmeMinmnMB1u-S3Ok0dwd1dRd1dRd1jReXg1YN27LdgH_HfnRRA7YGvfgPTf3Td2dXl4o_8F_Teoio</recordid><startdate>20180726</startdate><enddate>20180726</enddate><creator>Pradhan, Tapas R.</creator><creator>Kim, Hong Won</creator><creator>Park, Jin Kyoon</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6768-2788</orcidid></search><sort><creationdate>20180726</creationdate><title>Regiodivergent Synthesis of 1,3‐ and 1,4‐Enynes through Kinetically Favored Hydropalladation and Ligand‐Enforced Carbopalladation</title><author>Pradhan, Tapas R. ; Kim, Hong Won ; Park, Jin Kyoon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5468-d9c873fa7c392cf707f5f8b2a4c21d9dde5232deba2ebfa396eb424c60cd2f9c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alkaloids</topic><topic>Alkynes</topic><topic>Carbohydrates</topic><topic>carbopalladation</topic><topic>diastereoselectivity</topic><topic>divergent</topic><topic>hydropalladation</topic><topic>Ligands</topic><topic>Regioselectivity</topic><topic>Steroid hormones</topic><topic>Steroids</topic><topic>Vitamins</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pradhan, Tapas R.</creatorcontrib><creatorcontrib>Kim, Hong Won</creatorcontrib><creatorcontrib>Park, Jin Kyoon</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pradhan, Tapas R.</au><au>Kim, Hong Won</au><au>Park, Jin Kyoon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regiodivergent Synthesis of 1,3‐ and 1,4‐Enynes through Kinetically Favored Hydropalladation and Ligand‐Enforced Carbopalladation</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2018-07-26</date><risdate>2018</risdate><volume>57</volume><issue>31</issue><spage>9930</spage><epage>9935</epage><pages>9930-9935</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Pd‐catalyzed hydroalkynylations were developed that involve ligand‐enabled regiodivergent addition of an alkyne to an allenamide, giving branched and linear products stereoselectively and facilitated by the neighboring amide group. Regioselectivity was achieved with the use of (o‐OMePh)3P and BrettPhos, which allowed the functionalization of various alkynes, including steroids, carbohydrates, alkaloids, chiral ligands, and vitamins. Based on the experimental results, it was proposed that hydro‐ and carbopalladation processes operated during the formations of the branched and linear products, respectively.
Pd‐catalyzed hydroalkynylations involving ligand‐enabled regiodivergent addition of an alkyne to an allenamide stereoselectively gave branched and linear products facilitated by the neighboring amide group. Regioselectivity was achieved with the use of (o‐OMePh)3P and BrettPhos. Hydro‐ and carbopalladation processes were shown to operate during the formation of the branched and linear products, respectively.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29985561</pmid><doi>10.1002/anie.201805408</doi><tpages>6</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-6768-2788</orcidid></addata></record> |
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| subjects | Alkaloids Alkynes Carbohydrates carbopalladation diastereoselectivity divergent hydropalladation Ligands Regioselectivity Steroid hormones Steroids Vitamins |
| title | Regiodivergent Synthesis of 1,3‐ and 1,4‐Enynes through Kinetically Favored Hydropalladation and Ligand‐Enforced Carbopalladation |
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