5728-91-6Relevant academic research and scientific papers
Access to α-Cyano Carbonyls Bearing a Quaternary Carbon Center by Reductive Cyanation
Ren, Xinyi,Shen, Chaoren,Wang, Guangzhu,Shi, Zhanglin,Tian, Xinxin,Dong, Kaiwu
supporting information, p. 2527 - 2532 (2021/05/05)
Reductive cyanation of tertiary alkyl bromides using electrophilic cyanating reagent and zinc reductant was developed, providing various α-cyano ketones, esters, and carboxamides containing a nitrile-bearing all-carbon quaternary center in good to excellent yields under mild reaction conditions. The corresponding reaction mechanism involving in situ generated organozinc reagent and reactivity distinction was elucidated by density functional theory computation.
Iron-Catalyzed Acyl Migration of Tertiary α-Azidyl Ketones: Synthetic Approach toward Enamides and Isoquinolones
Yang, Tonghao,Fan, Xing,Zhao, Xiaopeng,Yu, Wei
supporting information, p. 1875 - 1879 (2018/04/16)
This paper reports that tertiary α-azidyl phenyl ketones can be transformed into enamides by treatment with FeBr2 at elevated temperature in DMF. The reaction proceeds via 1,2-benzoyl migration from α-carbon to the nitrogen atom, accompanied by expulsion of a nitrogen molecule. This protocol is suitable for the synthesis of N-(cyclopent-1-en-1-yl)benzamides, N-(cyclohex-1-en-1-yl)benzamides, and N-benzoyl-α-methyl enamines and provides a convenient approach toward isoquinolones.
METHODS OF PREPARING a,?-UNSATURATED OR a-HALO KETONES AND ALDEHYDES
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Paragraph 0116; 0117; 0130; 0131; 0134; 0135, (2017/07/14)
Copper(II) bromide mediated oxidation of acylated enol and use of the reaction in the synthesis of α,β-unsaturated or α-bromo ketones or aldehydes are disclosed. The method provides an efficient and practical process for manufacturing dehydrohedione (DHH) and many other versatile α,β-unsaturated or α-bromo ketones or aldehydes in large scales to avoid using precious metal compounds.
α,β-Unsaturated ketones via copper(II) bromide mediated oxidation
Sharley, James S.,Collado Pérez, Ana María,Ferri, Estela Espinos,Miranda, Amadeo Fernandez,Baxendale, Ian R.
, p. 2947 - 2954 (2016/05/19)
A protocol for effecting a rapid Saegusa-type oxidation of enol acetates is reported. This new method relies on the in situ elimination of an α-bromo intermediate to generate α,β-unsaturated ketones using copper(II) bromide. The methodology developed was applied to a range of substrates including a cyclohexanone, which could be directly converted to the corresponding phenol derivative. A catalytic system in which a non-masked ketone was successfully oxidised using substoichiometric CuBr2 was also developed as a proof of principle.
