74212-52-5Relevant articles and documents
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.
Transition-metal-free access to 7-azaindoles
Wang, Dong,Hu, Jianyong,Zhao, Junjie,Shen, Meng,Wang, Yuxi,Yu, Peng
supporting information, p. 4100 - 4110 (2018/06/25)
A novel method for transition-metal-free synthesis of 7-azaindoles is developed through a one-pot synthesis involving amination of pyridine N-oxides and intramolecular enamine formation. Remarkable features of the method include simple operation, mild reaction conditions, wide substrate scope, and easily accessible starting materials.
Conversion of Pyridines and Quinolines into Pyridazines and Pyrazoles
Baradarani, M. Mehdi,Joule, John A.
, p. 72 - 77 (2007/10/02)
3-Phenacylpyridinium and 3-phenacylquinolinium methiodides are shown to react with hydrazine-potassium hydroxide and hydrazine respectively to give 4-alkyl-6-phenylpyridazines and 4-(2-aminobenzyl)-6-phenylpyridazines respectively. 3-Benzoylpyridinium met