Controlled reduction of carboxamides to alcohols or amines by zinc hydrides
New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2 ). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives ami...
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sg-ntu-dr.10356-1446042023-02-28T19:29:00Z Controlled reduction of carboxamides to alcohols or amines by zinc hydrides Ong, Derek Yiren Yen, Zhihao Yoshii, Asami Imbernon, Julia Revillo Takita, Ryo Chiba, Shunsuke School of Physical and Mathematical Sciences Science::Chemistry Alcohols Amides New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2 ). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH2 )∞ is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H-Zn-Cl)2 is the key species for the production of amines. Ministry of Education (MOE) Accepted version This work was supported by funding from Nanyang Technological University (NTU) (for S.C.), the Singapore Ministry of Education (Academic Research Fund Tier 1: RG10/17 for S.C.), and Takeda Science Foundation (for R.T.). Computations were performed using Research Center for Computational Science at Okazaki, Japan. We thank Prof. Subodh G. Mhaisalkar (School of Materials Science and Engineering, NTU) and Prof. Han Sen Soo (School of Physical and Mathematical Sciences, NTU) for the assistance in powder X‐ray diffraction (XRD) experiments. 2020-11-16T01:39:29Z 2020-11-16T01:39:29Z 2019 Journal Article Ong, D. Y., Yen, Z., Yoshii, A., Imbernon, J. R., Takita, R., & Chiba, S. (2019). Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides. Angewandte Chemie International Edition, 58(15), 4992–4997. doi:10.1002/anie.201900233 1433-7851 https://hdl.handle.net/10356/144604 10.1002/anie.201900233 30761712 15 58 4992 4997 en Angewandte Chemie International Edition This is the accepted version of the following article: Ong, D. Y., Yen, Z., Yoshii, A., Imbernon, J. R., Takita, R., & Chiba, S. (2019). Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides. Angewandte Chemie International Edition, 58(15), 4992–4997., which has been published in final form at doi:10.1002/anie.201900233. This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy [https://authorservices.wiley.com/authorresources/Journal-Authors/licensing/self-archiving.html]. application/pdf |
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Science::Chemistry Alcohols Amides |
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Science::Chemistry Alcohols Amides Ong, Derek Yiren Yen, Zhihao Yoshii, Asami Imbernon, Julia Revillo Takita, Ryo Chiba, Shunsuke Controlled reduction of carboxamides to alcohols or amines by zinc hydrides |
| description |
New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2 ). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH2 )∞ is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H-Zn-Cl)2 is the key species for the production of amines. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Ong, Derek Yiren Yen, Zhihao Yoshii, Asami Imbernon, Julia Revillo Takita, Ryo Chiba, Shunsuke |
| format |
Article |
| author |
Ong, Derek Yiren Yen, Zhihao Yoshii, Asami Imbernon, Julia Revillo Takita, Ryo Chiba, Shunsuke |
| author_sort |
Ong, Derek Yiren |
| title |
Controlled reduction of carboxamides to alcohols or amines by zinc hydrides |
| title_short |
Controlled reduction of carboxamides to alcohols or amines by zinc hydrides |
| title_full |
Controlled reduction of carboxamides to alcohols or amines by zinc hydrides |
| title_fullStr |
Controlled reduction of carboxamides to alcohols or amines by zinc hydrides |
| title_full_unstemmed |
Controlled reduction of carboxamides to alcohols or amines by zinc hydrides |
| title_sort |
controlled reduction of carboxamides to alcohols or amines by zinc hydrides |
| publishDate |
2020 |
| url |
https://hdl.handle.net/10356/144604 |
| _version_ |
1759855356205334528 |