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Tandem Rh(III)-Catalyzed Oxidative Acylation of Secondary Benzamides with Aldehydes and Intramolecular Cyclization: The Direct Synthesis of 3-Hydroxyisoindolin-1-ones
The rhodium-catalyzed oxidative acylation between secondary benzamides and aryl aldehydes via sp2 C–H bond activation followed by an intramolecular cyclization is described. This method results in the direct and efficient synthesis of 3-hydroxyisoindolin-1-one building blocks.
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| Published in: | Organic letters 2012-02, Vol.14 (3), p.906-909 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a314t-b03ecad247c9d72e898ba5bde0b586c88fcd3cbc03d55b9280ad94d916ddf3b43 |
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| cites | cdi_FETCH-LOGICAL-a314t-b03ecad247c9d72e898ba5bde0b586c88fcd3cbc03d55b9280ad94d916ddf3b43 |
| container_end_page | 909 |
| container_issue | 3 |
| container_start_page | 906 |
| container_title | Organic letters |
| container_volume | 14 |
| creator | Sharma, Satyasheel Park, Eonjeong Park, Jihye Kim, In Su |
| description | The rhodium-catalyzed oxidative acylation between secondary benzamides and aryl aldehydes via sp2 C–H bond activation followed by an intramolecular cyclization is described. This method results in the direct and efficient synthesis of 3-hydroxyisoindolin-1-one building blocks. |
| doi_str_mv | 10.1021/ol2034228 |
| format | article |
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This method results in the direct and efficient synthesis of 3-hydroxyisoindolin-1-one building blocks.</description><subject>Acylation</subject><subject>Aldehydes - chemistry</subject><subject>Benzamides - chemistry</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>Hydroxylation</subject><subject>Indoles - chemical synthesis</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><subject>Rhodium - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNptkctu1DAUhi0EoqWw4AWQN4h2EfAlycTspsOlkSpVosM6cnxOFFeOXewEmnkgnpMMU2bF6lz06ZPO-Ql5zdl7zgT_EJxgMheiekJOeSFktmKFeHrsS3ZCXqR0xxhfNuo5ORFClFLx_JT83moPONBv_Xld1xfZRo_azTsEevNgQY_2J9K1md3SBU9DR2_RBA86zvQS_U4PFjDRX3bs6doB9vN-XJS09mPUQ3BoJqcj3czG2d1fy0e67ZF-shHNSG9nP_aYbNq7ZXY1QwwPs03BegjO-oxnwWN6SZ512iV89VjPyPcvn7ebq-z65mu9WV9nWvJ8zFom0WgQ-cooWAmsVNXqogVkbVGVpqo6A9K0hkkoilaJimlQOSheAnSyzeUZeXfw3sfwY8I0NoNNBp3THsOUGsWVKlYl35MXB9LEkFLErrmPdlj-0nDW7FNpjqks7JtH69QOCEfyXwwL8PYAaJOauzBFvxz5H9Ef-gqWYg</recordid><startdate>20120203</startdate><enddate>20120203</enddate><creator>Sharma, Satyasheel</creator><creator>Park, Eonjeong</creator><creator>Park, Jihye</creator><creator>Kim, In Su</creator><general>American Chemical Society</general><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>7X8</scope></search><sort><creationdate>20120203</creationdate><title>Tandem Rh(III)-Catalyzed Oxidative Acylation of Secondary Benzamides with Aldehydes and Intramolecular Cyclization: The Direct Synthesis of 3-Hydroxyisoindolin-1-ones</title><author>Sharma, Satyasheel ; Park, Eonjeong ; Park, Jihye ; Kim, In Su</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a314t-b03ecad247c9d72e898ba5bde0b586c88fcd3cbc03d55b9280ad94d916ddf3b43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Acylation</topic><topic>Aldehydes - chemistry</topic><topic>Benzamides - chemistry</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>Hydroxylation</topic><topic>Indoles - chemical synthesis</topic><topic>Molecular Structure</topic><topic>Oxidation-Reduction</topic><topic>Rhodium - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sharma, Satyasheel</creatorcontrib><creatorcontrib>Park, Eonjeong</creatorcontrib><creatorcontrib>Park, Jihye</creatorcontrib><creatorcontrib>Kim, In Su</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sharma, Satyasheel</au><au>Park, Eonjeong</au><au>Park, Jihye</au><au>Kim, In Su</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tandem Rh(III)-Catalyzed Oxidative Acylation of Secondary Benzamides with Aldehydes and Intramolecular Cyclization: The Direct Synthesis of 3-Hydroxyisoindolin-1-ones</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2012-02, Vol.14 (3), p.906-909 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_919957614 |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Acylation Aldehydes - chemistry Benzamides - chemistry Catalysis Cyclization Hydroxylation Indoles - chemical synthesis Molecular Structure Oxidation-Reduction Rhodium - chemistry Stereoisomerism |
| title | Tandem Rh(III)-Catalyzed Oxidative Acylation of Secondary Benzamides with Aldehydes and Intramolecular Cyclization: The Direct Synthesis of 3-Hydroxyisoindolin-1-ones |
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