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Ligand-Promoted Borylation of C(sp3)H Bonds with Palladium(II) Catalysts
A quinoline‐based ligand effectively promotes the palladium‐catalyzed borylation of C(sp3)H bonds. Primary β‐C(sp3)H bonds in carboxylic acid derivatives as well as secondary C(sp3)H bonds in a variety of carbocyclic rings, including cyclopropanes, cyclobutanes, cyclopentanes, cyclohexanes, and c...
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Published in: | Angewandte Chemie International Edition 2016-01, Vol.55 (2), p.785-789 |
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creator | He, Jian Jiang, Heng Takise, Ryosuke Zhu, Ru-Yi Chen, Gang Dai, Hui-Xiong Dhar, T. G. Murali Shi, Jun Zhang, Hao Cheng, Peter T. W. Yu, Jin-Quan |
description | A quinoline‐based ligand effectively promotes the palladium‐catalyzed borylation of C(sp3)H bonds. Primary β‐C(sp3)H bonds in carboxylic acid derivatives as well as secondary C(sp3)H bonds in a variety of carbocyclic rings, including cyclopropanes, cyclobutanes, cyclopentanes, cyclohexanes, and cycloheptanes, can thus be borylated. This directed borylation method complements existing iridium(I)‐ and rhodium(I)‐catalyzed CH borylation reactions in terms of scope and operational conditions.
A quinoline‐based ligand promotes the efficient palladium‐catalyzed borylation of primary β‐C(sp3)H bonds in carboxylic acid derivatives as well as secondary C(sp3)H bonds in a variety of carbocycles. This directed borylation method complements existing iridium(I)‐ and rhodium(I)‐catalyzed CH borylation reactions in terms of scope and reaction conditions. |
doi_str_mv | 10.1002/anie.201509996 |
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A quinoline‐based ligand promotes the efficient palladium‐catalyzed borylation of primary β‐C(sp3)H bonds in carboxylic acid derivatives as well as secondary C(sp3)H bonds in a variety of carbocycles. This directed borylation method complements existing iridium(I)‐ and rhodium(I)‐catalyzed CH borylation reactions in terms of scope and reaction conditions.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201509996</identifier><identifier>PMID: 26611496</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>amino acids ; Bonding ; Boron Compounds - chemistry ; borylation ; Carboxylic acids ; Catalysis ; Catalysts ; Chemical reactions ; CH activation ; Hydrogen Bonding ; Iridium ; Ligands ; Organic compounds ; Palladium ; Palladium - chemistry ; Quinoline ; Rhodium ; synthetic methods</subject><ispartof>Angewandte Chemie International Edition, 2016-01, Vol.55 (2), p.785-789</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5866-db9ef3f85a74fae5ee4df2fbacf8dc8e1cc32f713de5003faa6bf841bca0e6d3</citedby><cites>FETCH-LOGICAL-c5866-db9ef3f85a74fae5ee4df2fbacf8dc8e1cc32f713de5003faa6bf841bca0e6d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26611496$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>He, Jian</creatorcontrib><creatorcontrib>Jiang, Heng</creatorcontrib><creatorcontrib>Takise, Ryosuke</creatorcontrib><creatorcontrib>Zhu, Ru-Yi</creatorcontrib><creatorcontrib>Chen, Gang</creatorcontrib><creatorcontrib>Dai, Hui-Xiong</creatorcontrib><creatorcontrib>Dhar, T. G. Murali</creatorcontrib><creatorcontrib>Shi, Jun</creatorcontrib><creatorcontrib>Zhang, Hao</creatorcontrib><creatorcontrib>Cheng, Peter T. W.</creatorcontrib><creatorcontrib>Yu, Jin-Quan</creatorcontrib><title>Ligand-Promoted Borylation of C(sp3)H Bonds with Palladium(II) Catalysts</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A quinoline‐based ligand effectively promotes the palladium‐catalyzed borylation of C(sp3)H bonds. Primary β‐C(sp3)H bonds in carboxylic acid derivatives as well as secondary C(sp3)H bonds in a variety of carbocyclic rings, including cyclopropanes, cyclobutanes, cyclopentanes, cyclohexanes, and cycloheptanes, can thus be borylated. This directed borylation method complements existing iridium(I)‐ and rhodium(I)‐catalyzed CH borylation reactions in terms of scope and operational conditions.
A quinoline‐based ligand promotes the efficient palladium‐catalyzed borylation of primary β‐C(sp3)H bonds in carboxylic acid derivatives as well as secondary C(sp3)H bonds in a variety of carbocycles. This directed borylation method complements existing iridium(I)‐ and rhodium(I)‐catalyzed CH borylation reactions in terms of scope and reaction conditions.</description><subject>amino acids</subject><subject>Bonding</subject><subject>Boron Compounds - chemistry</subject><subject>borylation</subject><subject>Carboxylic acids</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical reactions</subject><subject>CH activation</subject><subject>Hydrogen Bonding</subject><subject>Iridium</subject><subject>Ligands</subject><subject>Organic compounds</subject><subject>Palladium</subject><subject>Palladium - chemistry</subject><subject>Quinoline</subject><subject>Rhodium</subject><subject>synthetic methods</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkc1u1DAURi0EakvbLUsUic10kcGO479lG5V2xKhU6khdWk58DS5JPLUTlXkeHoRH4hXIaMoIsYDVtXTPd3TlD6E3BM8JxsV703uYF5gwrJTiL9ARYQXJqRD05fQuKc2FZOQQvU7pYeKlxPwAHRacE1IqfoQ-Lv1n09v8NoYuDGCzixA3rRl86LPgsmqW1vTs5_cf19Oityl78sOX7Na0rbF-7GaLxVlWmcG0mzSkE_TKmTbB6fM8RqsPl6vqOl9-ulpU58u8YZLz3NYKHHWSGVE6AwygtK5wtWmctI0E0jS0cIJQCwxj6ozhtZMlqRuDgVt6jGY77TqGxxHSoDufGphO6iGMSRPBsWRKFWpC3_2FPoQx9tNxmiiCKcWE4n9SggkpmZRb13xHNTGkFMHpdfSdiRtNsN52obdd6H0XU-Dts3asO7B7_PfnT4DaAU--hc1_dPr8ZnH5pzzfZX0a4Ns-a-JXzQUVTN_fXOm7C1GtGOX6nv4CI_-k6A</recordid><startdate>20160111</startdate><enddate>20160111</enddate><creator>He, Jian</creator><creator>Jiang, Heng</creator><creator>Takise, Ryosuke</creator><creator>Zhu, Ru-Yi</creator><creator>Chen, Gang</creator><creator>Dai, Hui-Xiong</creator><creator>Dhar, T. G. Murali</creator><creator>Shi, Jun</creator><creator>Zhang, Hao</creator><creator>Cheng, Peter T. W.</creator><creator>Yu, Jin-Quan</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>7TM</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20160111</creationdate><title>Ligand-Promoted Borylation of C(sp3)H Bonds with Palladium(II) Catalysts</title><author>He, Jian ; Jiang, Heng ; Takise, Ryosuke ; Zhu, Ru-Yi ; Chen, Gang ; Dai, Hui-Xiong ; Dhar, T. G. Murali ; Shi, Jun ; Zhang, Hao ; Cheng, Peter T. W. ; Yu, Jin-Quan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5866-db9ef3f85a74fae5ee4df2fbacf8dc8e1cc32f713de5003faa6bf841bca0e6d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>amino acids</topic><topic>Bonding</topic><topic>Boron Compounds - chemistry</topic><topic>borylation</topic><topic>Carboxylic acids</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical reactions</topic><topic>CH activation</topic><topic>Hydrogen Bonding</topic><topic>Iridium</topic><topic>Ligands</topic><topic>Organic compounds</topic><topic>Palladium</topic><topic>Palladium - chemistry</topic><topic>Quinoline</topic><topic>Rhodium</topic><topic>synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>He, Jian</creatorcontrib><creatorcontrib>Jiang, Heng</creatorcontrib><creatorcontrib>Takise, Ryosuke</creatorcontrib><creatorcontrib>Zhu, Ru-Yi</creatorcontrib><creatorcontrib>Chen, Gang</creatorcontrib><creatorcontrib>Dai, Hui-Xiong</creatorcontrib><creatorcontrib>Dhar, T. G. Murali</creatorcontrib><creatorcontrib>Shi, Jun</creatorcontrib><creatorcontrib>Zhang, Hao</creatorcontrib><creatorcontrib>Cheng, Peter T. W.</creatorcontrib><creatorcontrib>Yu, Jin-Quan</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><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>He, Jian</au><au>Jiang, Heng</au><au>Takise, Ryosuke</au><au>Zhu, Ru-Yi</au><au>Chen, Gang</au><au>Dai, Hui-Xiong</au><au>Dhar, T. G. Murali</au><au>Shi, Jun</au><au>Zhang, Hao</au><au>Cheng, Peter T. W.</au><au>Yu, Jin-Quan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ligand-Promoted Borylation of C(sp3)H Bonds with Palladium(II) Catalysts</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-01-11</date><risdate>2016</risdate><volume>55</volume><issue>2</issue><spage>785</spage><epage>789</epage><pages>785-789</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>A quinoline‐based ligand effectively promotes the palladium‐catalyzed borylation of C(sp3)H bonds. Primary β‐C(sp3)H bonds in carboxylic acid derivatives as well as secondary C(sp3)H bonds in a variety of carbocyclic rings, including cyclopropanes, cyclobutanes, cyclopentanes, cyclohexanes, and cycloheptanes, can thus be borylated. This directed borylation method complements existing iridium(I)‐ and rhodium(I)‐catalyzed CH borylation reactions in terms of scope and operational conditions.
A quinoline‐based ligand promotes the efficient palladium‐catalyzed borylation of primary β‐C(sp3)H bonds in carboxylic acid derivatives as well as secondary C(sp3)H bonds in a variety of carbocycles. This directed borylation method complements existing iridium(I)‐ and rhodium(I)‐catalyzed CH borylation reactions in terms of scope and reaction conditions.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26611496</pmid><doi>10.1002/anie.201509996</doi><tpages>5</tpages><edition>International ed. in English</edition><oa>free_for_read</oa></addata></record> |
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subjects | amino acids Bonding Boron Compounds - chemistry borylation Carboxylic acids Catalysis Catalysts Chemical reactions CH activation Hydrogen Bonding Iridium Ligands Organic compounds Palladium Palladium - chemistry Quinoline Rhodium synthetic methods |
title | Ligand-Promoted Borylation of C(sp3)H Bonds with Palladium(II) Catalysts |
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