Bioinspired Synthesis of Nitriles from Primary Amides via Zinc/Anhydride Catalysis
A broad scope of aromatic and aliphatic primary amides were converted to their corresponding nitriles in high yields by using polymethylhydrosiloxane (PMHS) in the presence of catalytic amounts of ZnBr2 and propylphosphonic anhydride (T3P). As an example of dehydration reaction promoted by anhydride...
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| Published in: | Asian journal of organic chemistry Vol. 7; no. 2; pp. 367 - 370 |
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| Abstract | A broad scope of aromatic and aliphatic primary amides were converted to their corresponding nitriles in high yields by using polymethylhydrosiloxane (PMHS) in the presence of catalytic amounts of ZnBr2 and propylphosphonic anhydride (T3P). As an example of dehydration reaction promoted by anhydrides, ZnBr2 and T3P cooperatively activate the amide substrate and the silane to allow the desired dehydration to occur smoothly under mild conditions. Moreover, this method is suitable for the condensation reaction of carboxylic acids with amines to give the corresponding amide products, including a key intermediate of cinacalcet.
Thirsty? You must be dehydrated… As an example of dehydration reaction promoted by anhydrides, primary amides were efficiently converted to the corresponding nitriles by using polymethylhydrosiloxane (PMHS), and catalytic amounts of ZnBr2 and propylphosphonic anhydride (T3P). |
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| AbstractList | A broad scope of aromatic and aliphatic primary amides were converted to their corresponding nitriles in high yields by using polymethylhydrosiloxane (PMHS) in the presence of catalytic amounts of ZnBr
2
and propylphosphonic anhydride (T3P). As an example of dehydration reaction promoted by anhydrides, ZnBr
2
and T3P cooperatively activate the amide substrate and the silane to allow the desired dehydration to occur smoothly under mild conditions. Moreover, this method is suitable for the condensation reaction of carboxylic acids with amines to give the corresponding amide products, including a key intermediate of cinacalcet. A broad scope of aromatic and aliphatic primary amides were converted to their corresponding nitriles in high yields by using polymethylhydrosiloxane (PMHS) in the presence of catalytic amounts of ZnBr2 and propylphosphonic anhydride (T3P). As an example of dehydration reaction promoted by anhydrides, ZnBr2 and T3P cooperatively activate the amide substrate and the silane to allow the desired dehydration to occur smoothly under mild conditions. Moreover, this method is suitable for the condensation reaction of carboxylic acids with amines to give the corresponding amide products, including a key intermediate of cinacalcet. Thirsty? You must be dehydrated… As an example of dehydration reaction promoted by anhydrides, primary amides were efficiently converted to the corresponding nitriles by using polymethylhydrosiloxane (PMHS), and catalytic amounts of ZnBr2 and propylphosphonic anhydride (T3P). A broad scope of aromatic and aliphatic primary amides were converted to their corresponding nitriles in high yields by using polymethylhydrosiloxane (PMHS) in the presence of catalytic amounts of ZnBr2 and propylphosphonic anhydride (T3P). As an example of dehydration reaction promoted by anhydrides, ZnBr2 and T3P cooperatively activate the amide substrate and the silane to allow the desired dehydration to occur smoothly under mild conditions. Moreover, this method is suitable for the condensation reaction of carboxylic acids with amines to give the corresponding amide products, including a key intermediate of cinacalcet. |
| Author | Wang, Yuanyuan Qi, Huimin Chen, Shu‐Wei Fu, Liyan Li, Yuehui |
| Author_xml | – sequence: 1 givenname: Yuanyuan surname: Wang fullname: Wang, Yuanyuan organization: Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences – sequence: 2 givenname: Liyan surname: Fu fullname: Fu, Liyan organization: Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences – sequence: 3 givenname: Huimin surname: Qi fullname: Qi, Huimin organization: Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences – sequence: 4 givenname: Shu‐Wei surname: Chen fullname: Chen, Shu‐Wei email: chenshuwei2001@hotmail.com organization: Northwest A&F University – sequence: 5 givenname: Yuehui orcidid: 0000-0002-4520-1418 surname: Li fullname: Li, Yuehui email: yhli@licp.cas.cn organization: Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences |
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| Snippet | A broad scope of aromatic and aliphatic primary amides were converted to their corresponding nitriles in high yields by using polymethylhydrosiloxane (PMHS) in... |
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| StartPage | 367 |
| SubjectTerms | Aliphatic compounds Amides Amines Anhydrides Carboxylic acids Catalysis Chemical synthesis Condensates cooperative catalysis Dehydration hydrosilanes Nitriles Organic chemistry Substrates |
| Title | Bioinspired Synthesis of Nitriles from Primary Amides via Zinc/Anhydride Catalysis |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fajoc.201700664 https://www.proquest.com/docview/2001755101 |
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