Preparation of Unsymmetrical Ketones from Tosylhydrazones and Aromatic Aldehydes via Formyl C–H Bond Insertion
Preparation of ketones by insertion of diazo compounds into the formyl C–H bond of an aldehyde is an attractive procedure, but use of structurally diverse diazo compounds is hampered by preparation and safety issues. A convenient procedure for the synthesis of unsymmetrical ketones from bench-stable...
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| Veröffentlicht in: | Organic letters 2014-06, Vol.16 (11), p.3064-3067 |
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| container_end_page | 3067 |
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| container_issue | 11 |
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| container_title | Organic letters |
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| creator | Allwood, Daniel M Blakemore, David C Ley, Steven V |
| description | Preparation of ketones by insertion of diazo compounds into the formyl C–H bond of an aldehyde is an attractive procedure, but use of structurally diverse diazo compounds is hampered by preparation and safety issues. A convenient procedure for the synthesis of unsymmetrical ketones from bench-stable tosylhydrazones and aryl aldehydes is reported. The procedure can be performed in one pot from the parent carbonyl compound and needs only a base, with no additional promoters being required. |
| doi_str_mv | 10.1021/ol5011714 |
| format | Article |
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A convenient procedure for the synthesis of unsymmetrical ketones from bench-stable tosylhydrazones and aryl aldehydes is reported. 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Lett</addtitle><description>Preparation of ketones by insertion of diazo compounds into the formyl C–H bond of an aldehyde is an attractive procedure, but use of structurally diverse diazo compounds is hampered by preparation and safety issues. A convenient procedure for the synthesis of unsymmetrical ketones from bench-stable tosylhydrazones and aryl aldehydes is reported. The procedure can be performed in one pot from the parent carbonyl compound and needs only a base, with no additional promoters being required.</description><subject>Aldehydes - chemistry</subject><subject>Azo Compounds - chemistry</subject><subject>Catalysis</subject><subject>Hydrazones - chemistry</subject><subject>Hydrogen Bonding</subject><subject>Ketones - chemical synthesis</subject><subject>Ketones - chemistry</subject><subject>Molecular Structure</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkLFOwzAQhi0EoqUw8ALICxIMAduxW3ssFaWISjC0c-QkF5HKiYOdIoWJd-ANeRJcWjox3en-7_7T_QidU3JDCaO31ghC6YjyA9SngsXRiAh2uO-HpIdOvF-RAAmmjlGPcUmVHLE-al4cNNrptrQ1tgVe1r6rKmhdmWmDn6C1NXhcOFvhhfWdee1ypz9-h7rO8TgIYTfDY5ND0ML4vdR4al3VGTz5_vya4TsbwMfag9scOUVHhTYeznZ1gJbT-8VkFs2fHx4n43mkOR22Ua64TFMBIDjEwIp8SCgrmOSKMsrinEgpiFJpqpnmQkHMlMx4rijhMi6giAfoauvbOPu2Bt8mVekzMEbXYNc-oSLmRElOSECvt2jmrPcOiqRxZaVdl1CSbAJO9gEH9mJnu04ryPfkX6IBuNwCOvPJyq5dHb78x-gHlnCCrA</recordid><startdate>20140606</startdate><enddate>20140606</enddate><creator>Allwood, Daniel M</creator><creator>Blakemore, David C</creator><creator>Ley, Steven V</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>20140606</creationdate><title>Preparation of Unsymmetrical Ketones from Tosylhydrazones and Aromatic Aldehydes via Formyl C–H Bond Insertion</title><author>Allwood, Daniel M ; Blakemore, David C ; Ley, Steven V</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a416t-d948bb5ee54e3e2fd6012f284912123d0885099bba2a459e3298c4d910483fef3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Aldehydes - chemistry</topic><topic>Azo Compounds - chemistry</topic><topic>Catalysis</topic><topic>Hydrazones - chemistry</topic><topic>Hydrogen Bonding</topic><topic>Ketones - chemical synthesis</topic><topic>Ketones - chemistry</topic><topic>Molecular Structure</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Allwood, Daniel M</creatorcontrib><creatorcontrib>Blakemore, David C</creatorcontrib><creatorcontrib>Ley, Steven V</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>Allwood, Daniel M</au><au>Blakemore, David C</au><au>Ley, Steven V</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation of Unsymmetrical Ketones from Tosylhydrazones and Aromatic Aldehydes via Formyl C–H Bond Insertion</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2014-06, Vol.16 (11), p.3064-3067 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1534098400 |
| source | MEDLINE; ACS Publications |
| subjects | Aldehydes - chemistry Azo Compounds - chemistry Catalysis Hydrazones - chemistry Hydrogen Bonding Ketones - chemical synthesis Ketones - chemistry Molecular Structure |
| title | Preparation of Unsymmetrical Ketones from Tosylhydrazones and Aromatic Aldehydes via Formyl C–H Bond Insertion |
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