- Benzylic Aroylation of Toluenes Mediated by a LiN(SiMe3)2/Cs+System
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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.
- Gu, Yuanyun,Zhang, Zhen,Wang, Yan-En,Dai, Ziteng,Yuan, Yaqi,Xiong, Dan,Li, Jie,Walsh, Patrick J.,Mao, Jianyou
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supporting information
p. 406 - 418
(2022/01/14)
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- Azobenzene-Semicarbazone Enables Optical Control of Insect Sodium Channels and Behavior
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Photopharmacology uses molecular photoswitches to establish control over the action of bioactive molecules. The application of photopharmacology in the research of invertebrate sodium channels has not been investigated. Here we report several photochromic ligands of metaflumizone. One ligand, termed ABM04, underwent reversible trans-cis isomerization under ultraviolet or blue light irradiation. cis-ABM04 had excellent larvicidal activity against mosquito larvae with an LC50 value of 4.39 μM and showed insecticidal activity against Mythimna separata with an LC50 value of 7.19 μM. However, trans-ABM04 was not found to have biological activity. ABM04 (10 μM) can induce depolarization of dorsal unpaired median neurons and enable the real-time photoregulation of mosquito larval behavior. The precise regulation of invertebrate sodium channels is realized for the first time, which provides a new strategy for the basic and accurate research of invertebrate sodium channels.
- Chen, Ruijia,Fu, Wen,Li, Zhong,Qiao, Zhi,Shao, Xusheng,Xu, Zhiping,Zhang, Yongchao
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p. 15554 - 15561
(2021/12/27)
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- Synthesizing method of 1,2-phenylacetophenone and derivative thereof
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The invention discloses a synthesizing method of 1,2-phenylacetophenone and a derivative thereof. The synthesizing method comprises the following steps: (1) by using a compound I as an initiating raw material, generating amidating reaction with N,O-disubs
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- Containing 1, 2, 3-thiadiazole of the acetophenone derivatives and process for their preparation and use (by machine translation)
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The invention provides 4-cyanobenzyl-3-trifluoromethyl acetophenone derivatives containing 1,2,3-thiadiazole and a preparation method and use thereof. The invention relates to heterocyclic compounds containing 1,2,3-thiadiazole, wherein the heterocyclic compounds have a chemical structural general formula represented by a formula I shown in the specification. The invention discloses structural general formulae and synthesis methods of the compounds, use of the compounds serving as insecticides, acaricides and bactericides and processing processes for the compounds in the preparation of insecticides, acaricides and bactericides in a manner of being mixed with agriculturally acceptable auxiliaries or synergists. The invention further discloses use of the compounds in the prevention and control of the diseases, insect pests, mite pests and viral diseases of agriculture, forestry and horticulture in a manner of being combined with the commercial insecticides, acaricides, bactericides, plant virus resisting agents and plant activators and preparation methods of the compounds.
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Paragraph 0060; 0061; 0062
(2016/10/08)
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