Cobalt Catalyzed N‐Methylation of Amides using Methanol
N‐Methylation of amide with methanol is reported in the presence of an in‐situ generated cobalt catalyst. With this simple protocol, various amides were methylated in up to 99% yield. Notably, the involvement of active cobalt (I) hydride in this methylation process was revealed by control experiment...
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| Veröffentlicht in: | Asian journal of organic chemistry 2022-01, Vol.11 (1), p.n/a |
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| creator | Paul, Bhaskar Maji, Milan Panja, Dibyajyoti Kundu, Sabuj |
| description | N‐Methylation of amide with methanol is reported in the presence of an in‐situ generated cobalt catalyst. With this simple protocol, various amides were methylated in up to 99% yield. Notably, the involvement of active cobalt (I) hydride in this methylation process was revealed by control experiments. Deuterium labelling studies were carried out using methanol‐d4, taking benzamide and the possible intermediate N‐(hydroxymethyl)benzamide to understand this transformation. Additionally, DFT calculations for the amide−formaldehyde coupling were performed to elucidate the influence of catalyst in this step.
A cobalt catalyzed N‐methylation of amide using methanol is reported. Control experiments and DFT calculations were performed to realize this catalytic process |
| doi_str_mv | 10.1002/ajoc.202100678 |
| format | Article |
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A cobalt catalyzed N‐methylation of amide using methanol is reported. Control experiments and DFT calculations were performed to realize this catalytic process</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.202100678</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>amide ; Amides ; Benzamide ; Catalysts ; Cobalt ; control experiments and DFT calculations ; Deuterium ; Methanol ; methanol activation ; Methylation ; N-methylation ; Organic chemistry</subject><ispartof>Asian journal of organic chemistry, 2022-01, Vol.11 (1), p.n/a</ispartof><rights>2021 Wiley‐VCH GmbH</rights><rights>2022 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3578-441867f63c4618ad4187597e649b6d61dc512e5730ca8091368f13bdeb9e3c743</citedby><cites>FETCH-LOGICAL-c3578-441867f63c4618ad4187597e649b6d61dc512e5730ca8091368f13bdeb9e3c743</cites><orcidid>0000-0002-4976-6993 ; 0000-0002-4227-294X</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%2Fajoc.202100678$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.202100678$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Paul, Bhaskar</creatorcontrib><creatorcontrib>Maji, Milan</creatorcontrib><creatorcontrib>Panja, Dibyajyoti</creatorcontrib><creatorcontrib>Kundu, Sabuj</creatorcontrib><title>Cobalt Catalyzed N‐Methylation of Amides using Methanol</title><title>Asian journal of organic chemistry</title><description>N‐Methylation of amide with methanol is reported in the presence of an in‐situ generated cobalt catalyst. With this simple protocol, various amides were methylated in up to 99% yield. Notably, the involvement of active cobalt (I) hydride in this methylation process was revealed by control experiments. Deuterium labelling studies were carried out using methanol‐d4, taking benzamide and the possible intermediate N‐(hydroxymethyl)benzamide to understand this transformation. Additionally, DFT calculations for the amide−formaldehyde coupling were performed to elucidate the influence of catalyst in this step.
A cobalt catalyzed N‐methylation of amide using methanol is reported. Control experiments and DFT calculations were performed to realize this catalytic process</description><subject>amide</subject><subject>Amides</subject><subject>Benzamide</subject><subject>Catalysts</subject><subject>Cobalt</subject><subject>control experiments and DFT calculations</subject><subject>Deuterium</subject><subject>Methanol</subject><subject>methanol activation</subject><subject>Methylation</subject><subject>N-methylation</subject><subject>Organic chemistry</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFkMtOwzAQRS0EElXplnUk1ikeO34tq4inCt3A2nIcB1KlcYkTobDiE_hGvoREQWXJbGau5twZ6SJ0DngJGJNLs_V2STAZBBfyCM0IKBozCez4MGNxihYhbPFQQiggaoZU6jNTtVFqWlP1Hy6PHr8_vx5c-9pXpi19HfkiWu3K3IWoC2X9Eo07U_vqDJ0Upgpu8dvn6Pn66im9jdebm7t0tY4tZULGSQKSi4JTm3CQJh-kYEo4nqiM5xxyy4A4Jii2RmIFlMsCaJa7TDlqRULn6GK6u2_8W-dCq7e-a-rhpSacYAlA2UgtJ8o2PoTGFXrflDvT9BqwHhPSY0L6kNBgUJPhvaxc_w-tV_eb9M_7A4UjaJk</recordid><startdate>202201</startdate><enddate>202201</enddate><creator>Paul, Bhaskar</creator><creator>Maji, Milan</creator><creator>Panja, Dibyajyoti</creator><creator>Kundu, Sabuj</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-4976-6993</orcidid><orcidid>https://orcid.org/0000-0002-4227-294X</orcidid></search><sort><creationdate>202201</creationdate><title>Cobalt Catalyzed N‐Methylation of Amides using Methanol</title><author>Paul, Bhaskar ; Maji, Milan ; Panja, Dibyajyoti ; Kundu, Sabuj</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3578-441867f63c4618ad4187597e649b6d61dc512e5730ca8091368f13bdeb9e3c743</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>amide</topic><topic>Amides</topic><topic>Benzamide</topic><topic>Catalysts</topic><topic>Cobalt</topic><topic>control experiments and DFT calculations</topic><topic>Deuterium</topic><topic>Methanol</topic><topic>methanol activation</topic><topic>Methylation</topic><topic>N-methylation</topic><topic>Organic chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Paul, Bhaskar</creatorcontrib><creatorcontrib>Maji, Milan</creatorcontrib><creatorcontrib>Panja, Dibyajyoti</creatorcontrib><creatorcontrib>Kundu, Sabuj</creatorcontrib><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Paul, Bhaskar</au><au>Maji, Milan</au><au>Panja, Dibyajyoti</au><au>Kundu, Sabuj</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cobalt Catalyzed N‐Methylation of Amides using Methanol</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2022-01</date><risdate>2022</risdate><volume>11</volume><issue>1</issue><epage>n/a</epage><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>N‐Methylation of amide with methanol is reported in the presence of an in‐situ generated cobalt catalyst. With this simple protocol, various amides were methylated in up to 99% yield. Notably, the involvement of active cobalt (I) hydride in this methylation process was revealed by control experiments. Deuterium labelling studies were carried out using methanol‐d4, taking benzamide and the possible intermediate N‐(hydroxymethyl)benzamide to understand this transformation. Additionally, DFT calculations for the amide−formaldehyde coupling were performed to elucidate the influence of catalyst in this step.
A cobalt catalyzed N‐methylation of amide using methanol is reported. Control experiments and DFT calculations were performed to realize this catalytic process</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ajoc.202100678</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-4976-6993</orcidid><orcidid>https://orcid.org/0000-0002-4227-294X</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | amide Amides Benzamide Catalysts Cobalt control experiments and DFT calculations Deuterium Methanol methanol activation Methylation N-methylation Organic chemistry |
| title | Cobalt Catalyzed N‐Methylation of Amides using Methanol |
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