Catalyst‐ and Additive‐Free Chemoselective Transfer Hydrogenation of α‐Keto Amides to α‐Hydroxy Amides by Sodium Formate
A catalyst‐ and additive‐free chemoselective transfer hydrogenation of α‐keto amides to α‐hydroxy amides is easily achieved by using sodium formate as a hydrogen source. The utility of this method is demonstrated by gram‐scale synthesis and transformation of the resultant α‐hydroxy amides into polys...
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| Veröffentlicht in: | European journal of organic chemistry 2019-09, Vol.2019 (34), p.5985-5991 |
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| container_issue | 34 |
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| container_title | European journal of organic chemistry |
| container_volume | 2019 |
| creator | Hao, Feiyue Gu, Zhenyu Liu, Guyue Yao, Wubing Jiang, Huajiang Wu, Jiashou |
| description | A catalyst‐ and additive‐free chemoselective transfer hydrogenation of α‐keto amides to α‐hydroxy amides is easily achieved by using sodium formate as a hydrogen source. The utility of this method is demonstrated by gram‐scale synthesis and transformation of the resultant α‐hydroxy amides into polysubstituted acetamides and 2‐arylindole derivatives. Control experiments suggest that the NH group of α‐keto amides is crucial for the chemoselective reduction through the formation of hydrogen bonds.
A catalyst‐ and additive‐free chemoselective transfer hydrogenation of α‐keto amides to α‐hydroxy amides is easily achieved by using sodium formate as a hydrogen source. Control experiments suggest that the NH group of α‐keto amides is crucial for the chemoselective reduction through the formation of hydrogen bonds. |
| doi_str_mv | 10.1002/ejoc.201901073 |
| format | Article |
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A catalyst‐ and additive‐free chemoselective transfer hydrogenation of α‐keto amides to α‐hydroxy amides is easily achieved by using sodium formate as a hydrogen source. Control experiments suggest that the NH group of α‐keto amides is crucial for the chemoselective reduction through the formation of hydrogen bonds.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201901073</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Amides ; Catalysis ; Catalysts ; Chemical industry ; Hydrogen bonding ; Hydrogen bonds ; Hydrogen storage ; Hydrogenation ; Sodium formate ; Transfer hydrogenation ; α‐Hydroxy amides ; α‐Keto amides</subject><ispartof>European journal of organic chemistry, 2019-09, Vol.2019 (34), p.5985-5991</ispartof><rights>2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3173-ed89c7d0299ba5e050909ddd962c9244d9e94fbb2905bb36906605ca946ec8803</citedby><cites>FETCH-LOGICAL-c3173-ed89c7d0299ba5e050909ddd962c9244d9e94fbb2905bb36906605ca946ec8803</cites><orcidid>0000-0003-4459-1511</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%2Fejoc.201901073$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201901073$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Hao, Feiyue</creatorcontrib><creatorcontrib>Gu, Zhenyu</creatorcontrib><creatorcontrib>Liu, Guyue</creatorcontrib><creatorcontrib>Yao, Wubing</creatorcontrib><creatorcontrib>Jiang, Huajiang</creatorcontrib><creatorcontrib>Wu, Jiashou</creatorcontrib><title>Catalyst‐ and Additive‐Free Chemoselective Transfer Hydrogenation of α‐Keto Amides to α‐Hydroxy Amides by Sodium Formate</title><title>European journal of organic chemistry</title><description>A catalyst‐ and additive‐free chemoselective transfer hydrogenation of α‐keto amides to α‐hydroxy amides is easily achieved by using sodium formate as a hydrogen source. The utility of this method is demonstrated by gram‐scale synthesis and transformation of the resultant α‐hydroxy amides into polysubstituted acetamides and 2‐arylindole derivatives. Control experiments suggest that the NH group of α‐keto amides is crucial for the chemoselective reduction through the formation of hydrogen bonds.
A catalyst‐ and additive‐free chemoselective transfer hydrogenation of α‐keto amides to α‐hydroxy amides is easily achieved by using sodium formate as a hydrogen source. Control experiments suggest that the NH group of α‐keto amides is crucial for the chemoselective reduction through the formation of hydrogen bonds.</description><subject>Amides</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical industry</subject><subject>Hydrogen bonding</subject><subject>Hydrogen bonds</subject><subject>Hydrogen storage</subject><subject>Hydrogenation</subject><subject>Sodium formate</subject><subject>Transfer hydrogenation</subject><subject>α‐Hydroxy amides</subject><subject>α‐Keto amides</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkE1Ow0AMhSMEEqWwZT0S6xRP_r2sIkqBSl1QJHajScaBVE2mzKRAdogTcBUuwiE4CWnLz5KV7af32fJznGMOAw7gndJc5wMPOAKH2N9xehwQXYgQdrs-8AOXo3-77xxYOwcAjCLec15T2chFa5vPlzcma8WGSpVN-UjdPDJELL2nSltaUL5W2czI2hZk2LhVRt9RLZtS10wX7OO9Q66o0WxYlYos67qNtnE-tz9y1rJrrcpVxUbaVLKhQ2evkAtLR9-179yMzmbp2J1Mzy_S4cTNfR77LqkE81iBh5jJkCAEBFRKYeTl6AWBQsKgyDIPIcwyv3s7iiDMJQYR5UkCft852e5dGv2wItuIuV6ZujspPC_BgCeQxJ1rsHXlRltrqBBLU1bStIKDWOcs1jmL35w7ALfAU7mg9h-3OLucpn_sF7JSh_Q</recordid><startdate>20190915</startdate><enddate>20190915</enddate><creator>Hao, Feiyue</creator><creator>Gu, Zhenyu</creator><creator>Liu, Guyue</creator><creator>Yao, Wubing</creator><creator>Jiang, Huajiang</creator><creator>Wu, Jiashou</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-4459-1511</orcidid></search><sort><creationdate>20190915</creationdate><title>Catalyst‐ and Additive‐Free Chemoselective Transfer Hydrogenation of α‐Keto Amides to α‐Hydroxy Amides by Sodium Formate</title><author>Hao, Feiyue ; Gu, Zhenyu ; Liu, Guyue ; Yao, Wubing ; Jiang, Huajiang ; Wu, Jiashou</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3173-ed89c7d0299ba5e050909ddd962c9244d9e94fbb2905bb36906605ca946ec8803</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Amides</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical industry</topic><topic>Hydrogen bonding</topic><topic>Hydrogen bonds</topic><topic>Hydrogen storage</topic><topic>Hydrogenation</topic><topic>Sodium formate</topic><topic>Transfer hydrogenation</topic><topic>α‐Hydroxy amides</topic><topic>α‐Keto amides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hao, Feiyue</creatorcontrib><creatorcontrib>Gu, Zhenyu</creatorcontrib><creatorcontrib>Liu, Guyue</creatorcontrib><creatorcontrib>Yao, Wubing</creatorcontrib><creatorcontrib>Jiang, Huajiang</creatorcontrib><creatorcontrib>Wu, Jiashou</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hao, Feiyue</au><au>Gu, Zhenyu</au><au>Liu, Guyue</au><au>Yao, Wubing</au><au>Jiang, Huajiang</au><au>Wu, Jiashou</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalyst‐ and Additive‐Free Chemoselective Transfer Hydrogenation of α‐Keto Amides to α‐Hydroxy Amides by Sodium Formate</atitle><jtitle>European journal of organic chemistry</jtitle><date>2019-09-15</date><risdate>2019</risdate><volume>2019</volume><issue>34</issue><spage>5985</spage><epage>5991</epage><pages>5985-5991</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A catalyst‐ and additive‐free chemoselective transfer hydrogenation of α‐keto amides to α‐hydroxy amides is easily achieved by using sodium formate as a hydrogen source. The utility of this method is demonstrated by gram‐scale synthesis and transformation of the resultant α‐hydroxy amides into polysubstituted acetamides and 2‐arylindole derivatives. Control experiments suggest that the NH group of α‐keto amides is crucial for the chemoselective reduction through the formation of hydrogen bonds.
A catalyst‐ and additive‐free chemoselective transfer hydrogenation of α‐keto amides to α‐hydroxy amides is easily achieved by using sodium formate as a hydrogen source. Control experiments suggest that the NH group of α‐keto amides is crucial for the chemoselective reduction through the formation of hydrogen bonds.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201901073</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-4459-1511</orcidid></addata></record> |
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| ispartof | European journal of organic chemistry, 2019-09, Vol.2019 (34), p.5985-5991 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Amides Catalysis Catalysts Chemical industry Hydrogen bonding Hydrogen bonds Hydrogen storage Hydrogenation Sodium formate Transfer hydrogenation α‐Hydroxy amides α‐Keto amides |
| title | Catalyst‐ and Additive‐Free Chemoselective Transfer Hydrogenation of α‐Keto Amides to α‐Hydroxy Amides by Sodium Formate |
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