126266-77-1Relevant academic research and scientific papers
Benzylic Aroylation of Toluenes Mediated by a LiN(SiMe3)2/Cs+System
Gu, Yuanyun,Zhang, Zhen,Wang, Yan-En,Dai, Ziteng,Yuan, Yaqi,Xiong, Dan,Li, Jie,Walsh, Patrick J.,Mao, Jianyou
supporting information, p. 406 - 418 (2022/01/14)
Chemoselective deprotonative functionalization of benzylic C-H bonds is challenging, because the arene ring contains multiple aromatic C(sp2)-H bonds, which can be competitively deprotonated and lead to selectivity issues. Recently it was found that bimetallic [MN(SiMe3)2 M = Li, Na]/Cs+ combinations exhibit excellent benzylic selectivity. Herein, is reported the first deprotonative addition of toluenes to Weinreb amides mediated by LiN(SiMe3)2/CsF for the synthesis of a diverse array of 2-arylacetophenones. Surprisingly, simple methyl benzoates also react with toluenes under similar conditions to form 2-arylacetophenones without double addition to give tertiary alcohol products. This finding greatly increases the practicality and impact of this chemistry. Some challenging substrates with respect to benzylic deprotonations, such as fluoro and methoxy substituted toluenes, are selectively transformed to 2-aryl acetophenones. The value of benzylic deprotonation of 3-fluorotoluene is demonstrated by the synthesis of a key intermediate in the preparation of Polmacoxib.
An unusual chemoselective oxidation strategy by an unprecedented exploration of an electrophilic center of DMSO: A new facet to classical DMSO oxidation
Chebolu, Rajesh,Bahuguna, Ashish,Sharma, Reena,Mishra, Vivek Kumar,Ravikumar
, p. 15438 - 15441 (2015/10/20)
A conceptually new dimethyl sulfoxide (DMSO) based oxidation process without the use of any activator has been demonstrated for the oxidation of active methylenes and benzhydrols. The developed protocol utilizes the electrophilic center of DMSO for oxidation, which was unexplored before. Mechanistic investigation has confirmed that the source of oxygen is DMSO.
Arylation of α-pivaloxyl ketones with arylboronic reagents via Ni-catalyzed sp3 C-O activation
Huang, Kun,Li, Gang,Huang, Wei-Ping,Yu, Da-Gang,Shi, Zhang-Jie
, p. 7224 - 7226 (2011/08/09)
A Suzuki-Miyaura coupling of α-pivaloxyl ketones via Ni-catalyzed sp3 C-O activation to produce α-aryl ketones is developed. This study offers a convenient method to construct α-arylation products from readily available α-hydroxyl carbonyl compounds.
Palladium-catalyzed carbonylative suzuki coupling of benzyl halides with potassium aryltrifluoroborates in aqueous media
Wu, Xiao-Feng,Neumann, Helfried,Beller, Matthias
experimental part, p. 788 - 792 (2011/05/15)
A general palladium-catalyzed carbonylative cross-coupling reaction of benzyl chlorides with potassium aryltrifluoroborates in water has been developed. Applying this improved methodology 16 different 1,2-diarylethanones have been synthesized in 40-89% yield. Copyright
NOVEL DIHYDROPYRIMIDIN-2(1H)-ONE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS
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Page/Page column 144, (2011/04/24)
The present invention is directed to novel dihydropyrimidin-2(1H)-one compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.
Tetralone acids as intermediates for the synthesis of podophyllotoxin analogues
Basavaraju,Anjanamurthy
, p. 876 - 880 (2007/10/03)
Tetralone acids 6, 7 and 8 have been synthesised as intermediates for the synthesis of podophyllotoxin analogues 3, 4 and 5. The possible steric hindrance of cyclohexyl group on the intramolecular Friedel-Crafts acylation reaction of anhydrides 15 b,c to tetralone acids 7 and 8 is also discussed here.
The reaction of arylaldehydes with hexamethylphosphorous triamide and the use of the resulting products for the synthesis of enamines and deoxybenzoins
Babudri,Fiandanese,Musio,Naso,Sciavovelli,Scilimati
, p. 225 - 228 (2007/10/02)
The reaction between the arylaldehydes 1a,b and hexamethylphosphorous triamide 2 leads to the [aryl(dimethylamino)methyl]phosphonic bis(dimethylamides) 3a,b. These can be easily deprotonated by butyllithium in 1,2-dimethoxyethane and condensed with arylaldehydes to afford enamines 4a-f or deoxybenzoins 5a-f in fair to good yield.
