Gu, Yuanyun; Zhang, Zhen; Wang, Yan-En; Dai, Ziteng; Yuan, Yaqi; Xiong, Dan; Li, Jie; Walsh, Patrick J.; Mao, Jianyou published the artcile< Benzylic Aroylation of Toluenes Mediated by a LiN(SiMe3)2/Cs+ System>, Related Products of 2557-13-3, the main research area is aryl acetophenone preparation; methyl benzoate Weinreb amide toluene benzylic aroylation.
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 Me benzoates also react with toluenes under similar conditions to form 2-arylacetophenones without double addition to give tertiary alc. products. This finding greatly increases the practicality and impact of this chem. 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.
Journal of Organic Chemistry published new progress about Acetophenones Role: SPN (Synthetic Preparation), PREP (Preparation) (2-aryl). 2557-13-3 belongs to class esters-buliding-blocks, and the molecular formula is C9H7F3O2, Related Products of 2557-13-3.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics