7274-71-7Relevant articles and documents
Substituent-induced delocalization effects on hydrogen-bonding interaction in poly(N-phenyl methacrylamide) derivatives
Kuo, Shiao-Wei,Lin, Chien-Ting,Chen, Jem-Kun,Ko, Fu-Hsiang,Chang, Feng-Chih,Jeong, Kwang-Un
, p. 2600 - 2608 (2011)
Within small molecules, the hydrogen-bonding behaviors affected by delocalization have been studied thoroughly, but rare publication in macromolecules. Therefore, three poly(N-phenyl methacrylamide)s, poly(N-phenyl methacrylamide) (PNPAA), poly(N-4-methox
Bromo Radical-Mediated Photoredox Aldehyde Decarbonylation towards Transition-Metal-Free Hydroalkylation of Acrylamides at Room Temperature
Sun, Zhaozhao,Huang, Huawen,Wang, Qiaolin,Deng, Guo-Jun
supporting information, p. 453 - 458 (2021/12/03)
Herein, we report a visible-light-mediated hydroalkylation reaction of alkenes using easily available aldehydes as alkyl sources via bromo radical-promoted photoredox decarbonylation. This protocol provides an alternative entry to C(sp3)?C(sp3) bond formation and features considerable advantages including mild and clean reaction conditions, obviation for transition-metal catalyst, and good functional group compatibility.
Reactions of 2,3-Dibromo-2-methylpropanamides Promoted by Potassium tert-Butoxide
Galeeva, A. M.,Miftakhov, M. S.,Selezneva, N. K.,Valiullina, Z. R.
, p. 1643 - 1649 (2021/12/13)
Abstract: 2,3-Dibromo-2-methylpropanamides with different substituents on the nitrogen atom were synthe-sized, and their transformations by the action of potassium tert-butoxide in THF were studied. 2,3-Dibromo-N-(4-methoxyphenyl)-2-methylpropanamide and 2,3-dibromo-N-(2,5-dibromo-4-methoxyphenyl)-2-methyl-propan-amide reacted with 1–2 equiv of t-BuOK to give the corresponding N-substituted 3-bromo-3-methyl- and 3-methylideneazetidin-2-ones with acceptable yields and selectivity. Increase of the amount of t-BuOK to 3–5 equiv led to significant reduction of the yield of vinyl bromides and 3-methylideneazetidin-2-ones. On the other hand, the reaction of 2,3-dibromo-N-(tert-butyl)-2-methylpropanamide with t-BuOK afforded 3-(tert-bu-toxymethyl)-1-tert-butylazetidin-2-one with a good yield and selectivity.
Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals
Das, Sanju,De Sarkar, Suman,Mandal, Tanumoy
supporting information, (2021/12/10)
A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.
