Formation of Amides from Imines via Cyanide-Mediated Metal-Free Aerobic Oxidation
A new protocol for the direct formation of amides from imines derived from aromatic aldehydes via metal-free aerobic oxidation in the presence of cyanide is described. This protocol was applicable to various aldimines, and the desired amides were obtained in moderate to good yields. Mechanistic stud...
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| Veröffentlicht in: | Journal of organic chemistry 2015-12, Vol.80 (24), p.11993-11998 |
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| Sprache: | eng |
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| container_end_page | 11998 |
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| container_issue | 24 |
| container_start_page | 11993 |
| container_title | Journal of organic chemistry |
| container_volume | 80 |
| creator | Seo, Hong-Ahn Cho, Yeon-Ho Lee, Ye-Sol Cheon, Cheol-Hong |
| description | A new protocol for the direct formation of amides from imines derived from aromatic aldehydes via metal-free aerobic oxidation in the presence of cyanide is described. This protocol was applicable to various aldimines, and the desired amides were obtained in moderate to good yields. Mechanistic studies suggested that this aerobic oxidative amidation might proceed via the addition of cyanide to imines followed by proton transfer from carbon to nitrogen in the original imines, leading to carbanions of α-amino nitriles, which undergo subsequent oxidation with molecular oxygen in air to provide the desired amide compounds. |
| doi_str_mv | 10.1021/acs.joc.5b01922 |
| format | Article |
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This protocol was applicable to various aldimines, and the desired amides were obtained in moderate to good yields. Mechanistic studies suggested that this aerobic oxidative amidation might proceed via the addition of cyanide to imines followed by proton transfer from carbon to nitrogen in the original imines, leading to carbanions of α-amino nitriles, which undergo subsequent oxidation with molecular oxygen in air to provide the desired amide compounds.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.5b01922</identifier><identifier>PMID: 26580330</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2015-12, Vol.80 (24), p.11993-11998</ispartof><rights>Copyright © 2015 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-5bdc8a61d917c1e59872b1cf13554ab1a1892cf0e1d6e656371b1a0f52f7386f3</citedby><cites>FETCH-LOGICAL-a333t-5bdc8a61d917c1e59872b1cf13554ab1a1892cf0e1d6e656371b1a0f52f7386f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.5b01922$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.5b01922$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2764,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26580330$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Seo, Hong-Ahn</creatorcontrib><creatorcontrib>Cho, Yeon-Ho</creatorcontrib><creatorcontrib>Lee, Ye-Sol</creatorcontrib><creatorcontrib>Cheon, Cheol-Hong</creatorcontrib><title>Formation of Amides from Imines via Cyanide-Mediated Metal-Free Aerobic Oxidation</title><title>Journal of organic chemistry</title><addtitle>J. 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| source | ACS Publications |
| title | Formation of Amides from Imines via Cyanide-Mediated Metal-Free Aerobic Oxidation |
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