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

doi:10.1002/ange.201900233

“…developed a strategy for the controlled reduction of carboxamides 157 to alcohols 158 or amines 159 employing zinc hydride, generated in situ by combining sodium hydride (NaH) and zinc halides (ZnX 2 ) (Scheme 27). [56] The nature of the halide on ZnX 2 was shown to afford different zinc hydride species, dictating the selectivity of the reduction. In the NaH−ZnI 2 system, polymeric zinc hydride (ZnH 2 ) is generated, delivering alcohols.…”

Section: Other Strategies For Amide Functionalisationmentioning

confidence: 99%

Challenges and Breakthroughs in Selective Amide Activation

Feng

¹

,

Zhang

²

,

Maulide

³

2022

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In contrast to ketones and carboxylic esters, amides are classically seen as comparatively unreactive members of the carbonyl family, owing to their unique structural and electronic features. However, recent decades have seen the emergence of research programmes focused on the selective activation of amides under mild conditions. In the past four years, this area has continued to rapidly develop, with new advances coming in at a fast pace. Several novel activation strategies have been demonstrated as effective tools for selective amide activation, enabling transformations that are at once synthetically useful and mechanistically intriguing. This Minireview comprises recent advances in the field, highlighting new trends and breakthroughs in what could be called a new age of amide activation.

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Hydromagnesiation of 1,3‐Enynes by Magnesium Hydride for Synthesis of Tri‐ and Tetra‐substituted Allenes

Wang

¹

,

Pang

²

,

Watanabe

³

et al. 2020

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A protocol for regio-controlled hydromagnesiation of 1,3-enynes was developed using magnesium hydride that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI 2) in THF. The resulting allenylmagnesium species could be converted into tri-and tetra-substituted allenes by subsequent treatment with various carbon-and silicon-based electrophiles with the aid of CuCN as a catalyst.

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Challenges and Breakthroughs in Selective Amide Activation

Feng

¹

,

Zhang

²

,

Maulide

³

2022

Angewandte Chemie

4

0

View full text Add to dashboard Cite

In contrast to ketones and carboxylic esters, amides are classically seen as comparatively unreactive members of the carbonyl family, owing to their unique structural and electronic features. However, recent decades have seen the emergence of research programmes focused on the selective activation of amides under mild conditions. In the past four years, this area has continued to rapidly develop, with new advances coming in at a fast pace. Several novel activation strategies have been demonstrated as effective tools for selective amide activation, enabling transformations that are at once synthetically useful and mechanistically intriguing. This Minireview comprises recent advances in the field, highlighting new trends and breakthroughs in what could be called a new age of amide activation.

show abstract

Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides

Cited by 7 publications

References 62 publications

Challenges and Breakthroughs in Selective Amide Activation

Challenges and Breakthroughs in Selective Amide Activation

Hydromagnesiation of 1,3‐Enynes by Magnesium Hydride for Synthesis of Tri‐ and Tetra‐substituted Allenes

Challenges and Breakthroughs in Selective Amide Activation

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