2430-99-1Relevant articles and documents
H2O2-mediated room temperature synthesis of 2-arylacetophenones from arylhydrazines and vinyl azides in water
Luo, Mengqiang,Zhang, Yaohong,Fang, Ping,Li, Yan,Qi, Chenze,Li, Yong,Shen, Runpu,Cheng, Kai,Wang, Hai
supporting information, p. 630 - 635 (2022/02/01)
An environmentally benign, cost-efficient and practical methodology for the room temperature synthesis of 2-arylacetophenones in water has been discovered. The facile and efficient transformation involves the oxidative radical addition of arylhydrazines with α-aryl vinyl azides in the presence of H2O2 (as a radical initiator) and PEG-800 (as a phase-transfer catalyst). From the viewpoint of green chemistry and organic synthesis, the present protocol is of great significance because of using cheap, non-toxic and readily available starting materials and reagents as well as amenability to gram-scale synthesis, which provides an attractive strategy to access 2-arylacetophenones.
The organocatalytic enantiodivergent fluorination of β-ketodiaryl-phosphine oxides for the construction of carbon-fluorine quaternary stereocenters
Xie, Shaolei,He, Zhi-Juan,Zhang, Ling-Hui,Huang, Bo-Lun,Chen, Xiao-Wei,Zhan, Zong-Song,Zhang, Fu-Min
supporting information, p. 2069 - 2072 (2021/03/01)
Commercially available cinchona alkaloids that can catalyze the enantiodivergent fluorination of β-ketodiarylphosphine oxides were developed to construct carbon-fluorine quaternary stereocenters. This protocol features a wide scope of substrates and excellent enantioselectivities, and it is scalable.
Benzylic aroylation of toluenes with unactivated tertiary benzamides promoted by directed ortho-lithiation
Bao, Can-Can,Luo, Yan-Long,Du, Hui-Zhen,Guan, Bing-Tao
, p. 1349 - 1354 (2021/07/12)
The deprotonative functionalization of toluenes, for their weak acidity, generally needs strong bases, thus leading to the requirement of harsh conditions and the generation of by-products. Direct nucleophilic acyl substitution reaction of amides with organometallic reagents could provide an ideal solution for ketone synthesis. However, the inert amides and highly reactive organometallic reagents bring great challenges for an efficient and selective synthetic approach. Herein, we reported an lithium diisopropylamide (LDA)-promoted benzylic aroylation of toluenes with unactivated tertiary benzamides, providing a direct and efficient synthesis of various aryl benzyl ketones. This process features a kinetic deprotonative functionalization of toluenes with a readily available base LDA. Mechanism studies revealed that the directed ortho-lithiation of the tertiary benzamide with LDA promoted the benzylic kinetic deprotonation of toluene and triggered the nucleophilic acyl substitution reaction with the amide. [Figure not available: see fulltext.].