3669-48-5Relevant 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.
Exploring Tandem Ruthenium-Catalyzed Hydrogen Transfer and SNAr Chemistry
Polidano, Kurt,Reed-Berendt, Benjamin G.,Basset, Ana?s,Watson, Andrew J. A.,Williams, Jonathan M. J.,Morrill, Louis C.
supporting information, p. 6716 - 6719 (2017/12/26)
A hydrogen-transfer strategy for the catalytic functionalization of benzylic alcohols via electronic arene activation, accessing a diverse range of bespoke diaryl ethers and aryl amines in excellent isolated yields (38 examples, 70% average yield), is reported. Taking advantage of the hydrogen-transfer approach, the oxidation level of the functionalized products can be selected by judicious choice of simple and inexpensive additives.
An improved synthesis of bis(cyclopentadienone)
Yu, Ming Ming,Li, Xia,Luan, Miao,Gao, Jun Na,Shi, Qiu Zhi,Tang, Ming Sheng,Wei, Liu He
experimental part, p. 1157 - 1161 (2011/10/08)
An improved strategy for the synthesis of 3,3′-(oxy-p-phenylene)bis(2,4,5-triphenylcyclopentadienone) was developed, which includes three steps: Friedel-Crafts reaction, oxidation and condensation. Importantly, the use of KMnO4 made the second step simple and efficient, which has potential application to synthesis of bis(cyclopentadienone)s. The course of oxidation has been confirmed by isolated intermediates.
