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Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides
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- Derek Yiren Ong
- Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 Singapore
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- Zhihao Yen
- Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 Singapore
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- Asami Yoshii
- Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 Singapore
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- Julia Revillo Imbernon
- Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 Singapore
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- Ryo Takita
- Graduate School of Pharmaceutical Sciences The University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113-0033 Japan
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- Shunsuke Chiba
- Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore 637371 Singapore
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Description
<jats:title>Abstract</jats:title><jats:p>New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX<jats:sub>2</jats:sub>). Use of a different halide on ZnX<jats:sub>2</jats:sub> dictates the selectivity, wherein the NaH‐ZnI<jats:sub>2</jats:sub> system delivers alcohols and NaH‐ZnCl<jats:sub>2</jats:sub> gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH<jats:sub>2</jats:sub>)<jats:sub>∞</jats:sub> is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H−Zn−Cl)<jats:sub>2</jats:sub> is the key species for the production of amines.</jats:p>
Journal
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- Angewandte Chemie International Edition
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Angewandte Chemie International Edition 58 (15), 4992-4997, 2019-03-05
Wiley
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Details 詳細情報について
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- CRID
- 1360855569347165952
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- ISSN
- 15213773
- 15213757
- 14337851
- 00448249
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- HANDLE
- 10356/144604
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- PubMed
- 30761712
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- Web Site
- https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.201900233
- https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.201900233
- https://onlinelibrary.wiley.com/doi/full-xml/10.1002/anie.201900233
- https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fange.201900233
- https://onlinelibrary.wiley.com/doi/pdf/10.1002/ange.201900233
- https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ange.201900233
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