A Room Temperature Negishi Cross-Coupling Approach to C-Alkyl Glycosides
Glycosyl halides serve as effective alkyl halides for room temperature Negishi cross-coupling reactions using functionalized alkyl zinc reagents. The catalyst for these reactions is in situ generated (PyBox)NiCl2. The functional group tolerance on the zinc reagent is typically high, and both benzyl...
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| Veröffentlicht in: | Journal of the American Chemical Society 2007-02, Vol.129 (7), p.1908-1909 |
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| container_end_page | 1909 |
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| container_issue | 7 |
| container_start_page | 1908 |
| container_title | Journal of the American Chemical Society |
| container_volume | 129 |
| creator | Gong, Hegui Sinisi, Riccardo Gagné, Michel R |
| description | Glycosyl halides serve as effective alkyl halides for room temperature Negishi cross-coupling reactions using functionalized alkyl zinc reagents. The catalyst for these reactions is in situ generated (PyBox)NiCl2. The functional group tolerance on the zinc reagent is typically high, and both benzyl and ester protecting groups on the carbohydrate are tolerated. Anomer selectivities are modest for glucosyl halides but high for mannosyl halides. |
| doi_str_mv | 10.1021/ja068950t |
| format | Article |
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The catalyst for these reactions is in situ generated (PyBox)NiCl2. The functional group tolerance on the zinc reagent is typically high, and both benzyl and ester protecting groups on the carbohydrate are tolerated. 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Am. Chem. Soc</addtitle><description>Glycosyl halides serve as effective alkyl halides for room temperature Negishi cross-coupling reactions using functionalized alkyl zinc reagents. The catalyst for these reactions is in situ generated (PyBox)NiCl2. The functional group tolerance on the zinc reagent is typically high, and both benzyl and ester protecting groups on the carbohydrate are tolerated. Anomer selectivities are modest for glucosyl halides but high for mannosyl halides.</description><subject>Alkylation</subject><subject>Glucose - analogs & derivatives</subject><subject>Glycosides - chemical synthesis</subject><subject>Hydrocarbons, Chlorinated - chemistry</subject><subject>Hydrocarbons, Halogenated - chemistry</subject><subject>Monosaccharides - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Temperature</subject><subject>Zinc - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkDFPwzAQhS0EoqUw8AdQFpAYAraTOMkYImiRSoFSFhbLduw2bVIHO5Hov8dVq7IwnZ7u07t7D4BLBO8QxOh-ySBJ0gi2R6CPIgz9CGFyDPoQQuzHCQl64MzapZMhTtAp6KEYE-RkH4wyb6p17c1k3UjD2s5IbyLnpV2UXm60tX6uu6Yq13MvaxqjmVh4rfZyP6tWm8obVhuhbVlIew5OFKusvNjPAfh8epzlI3_8OnzOs7HPQhS3foR5EfEw5lJBjhSGgcBQkYjHIedFnAQkDVWoeEISxZVihShIAbfhCiwEk8EA3Ox83TPfnbQtrUsrZFWxtdSdpSR1KUmQOvB2B4ptDCMVbUxZM7OhCNJtbfRQm2Ov9qYdr2XxR-57coC_A0rbyp_DnpkVJXEQR3T29kFn6OX9azp5oInjr3c8E5YudWfWrpN_Dv8CzKGDPA</recordid><startdate>20070221</startdate><enddate>20070221</enddate><creator>Gong, Hegui</creator><creator>Sinisi, Riccardo</creator><creator>Gagné, Michel R</creator><general>American Chemical Society</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>7X8</scope></search><sort><creationdate>20070221</creationdate><title>A Room Temperature Negishi Cross-Coupling Approach to C-Alkyl Glycosides</title><author>Gong, Hegui ; Sinisi, Riccardo ; Gagné, Michel R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a417t-52bd5b47bef0b1f203c20f65b74bbd783694f4fb868fbffadcd6d08950d2ccae3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Alkylation</topic><topic>Glucose - analogs & derivatives</topic><topic>Glycosides - chemical synthesis</topic><topic>Hydrocarbons, Chlorinated - chemistry</topic><topic>Hydrocarbons, Halogenated - chemistry</topic><topic>Monosaccharides - chemical synthesis</topic><topic>Pyridines - chemistry</topic><topic>Temperature</topic><topic>Zinc - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gong, Hegui</creatorcontrib><creatorcontrib>Sinisi, Riccardo</creatorcontrib><creatorcontrib>Gagné, Michel R</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>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gong, Hegui</au><au>Sinisi, Riccardo</au><au>Gagné, Michel R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Room Temperature Negishi Cross-Coupling Approach to C-Alkyl Glycosides</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2007-02-21</date><risdate>2007</risdate><volume>129</volume><issue>7</issue><spage>1908</spage><epage>1909</epage><pages>1908-1909</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Glycosyl halides serve as effective alkyl halides for room temperature Negishi cross-coupling reactions using functionalized alkyl zinc reagents. The catalyst for these reactions is in situ generated (PyBox)NiCl2. The functional group tolerance on the zinc reagent is typically high, and both benzyl and ester protecting groups on the carbohydrate are tolerated. Anomer selectivities are modest for glucosyl halides but high for mannosyl halides.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>17261000</pmid><doi>10.1021/ja068950t</doi><tpages>2</tpages></addata></record> |
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| issn | 0002-7863 1520-5126 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Alkylation Glucose - analogs & derivatives Glycosides - chemical synthesis Hydrocarbons, Chlorinated - chemistry Hydrocarbons, Halogenated - chemistry Monosaccharides - chemical synthesis Pyridines - chemistry Temperature Zinc - chemistry |
| title | A Room Temperature Negishi Cross-Coupling Approach to C-Alkyl Glycosides |
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