3333-13-9Relevant articles and documents
Aryl C-F bond functionalization preparation method
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Paragraph 0052; 0054-0057, (2021/09/29)
The invention relates to the technical field of organic compound synthesis, in particular to an aryl C-F bond functionalization preparation method. A fluorobenzene compound and a nucleophilic reagent react under the action of a composite catalyst, wherein the composite catalyst is formed by mixing a visible light catalyst and a metal catalyst. The photocatalyst is adopted, the reaction process is safe and controllable, and operation in the preparation and production process is simplified; a purple LED is used as a reaction energy source and is green and environment-friendly, the energy utilization rate is high, and conversion from light energy to chemical energy can be efficiently realized; in the reaction, a simple nucleophilic reagent is used for attacking free radical cation species generated under a visible light catalysis condition, so that a target product with an extremely wide range is efficiently and greenly prepared; the operation steps are simplified, and the reaction route is shortened; and moreover, the forward reaction rate is high, and the production efficiency is remarkably improved.
Manganese catalyzed dehydrogenative silylation of alkenes: Direct access to allylsilanes
Wu, Shang,Zhang, Ying,Jiang, Hongyan,Ding, Ning,Wang, Yanbin,Su, Qiong,Zhang, Hong,Wu, Lan,Yang, Quanlu
supporting information, (2020/06/03)
Dehydrogenative silylation of alkenes with silanes to produce allylsilanes is achieved through manganese catalysis with a wide scope of substrate tolerance. This transformation involves silane radicals initiated by manganese complex without additional oxidant additives. It offers a general, convenient and practical protocol with excellent functional group compatibility and gram-scale capacity for the modular synthesis of allylsilanes.
Palladium-catalyzed allylic C-H oxidation under simple operation and mild conditions
Guo, Yunlong,Shen, Zengming
supporting information, p. 3103 - 3107 (2019/03/26)
We discovered an effective and simple system (Pd/BQ/air/r.t.) for making allylic alcohols through Pd-catalyzed allylic C-H bond functionalization. This approach exhibits advantages due to its simple operation, mild conditions, and environmentally benign features. By modifying reaction conditions, it can be suitable for preparing unsaturated aldehydes, allylic esters, ethers, and amines.
SO2 conversion to sulfones: Development and mechanistic insights of a sulfonylative Hiyama cross-coupling
Adenot, Aurélien,Char, Jo?lle,Von Wolff, Niklas,Lefèvre, Guillaume,Anthore-Dalion, Lucile,Cantat, Thibault
supporting information, p. 12924 - 12927 (2019/11/05)
A Pd-catalyzed Hiyama cross-coupling reaction using SO2 is described. The use of silicon-based nucleophiles leads to the formation of allyl sulfones under mild conditions with a broad functional group tolerance. Control experiments coupled with DFT calculations shed light on the key steps of the reaction mechanism, revealing the crucial role of a transient sulfinate anion.
Controllable, Sequential, and Stereoselective C-H Allylic Alkylation of Alkenes
Qin, Ling,Sharique, Mohammed,Tambar, Uttam K.
supporting information, p. 17305 - 17313 (2019/11/03)
The direct conversion of C-H bonds into new C-C bonds represents a powerful approach to generate complex molecules from simple starting materials. However, a general and controllable method for the sequential conversion of a methyl group into a fully substituted carbon center remains a challenge. We report a new method for the selective and sequential replacement of three C-H bonds at the allylic position of propylene and other simple terminal alkenes with different carbon groups derived from Grignard reagents. A copper catalyst and electron-rich biaryl phosphine ligand facilitate the formation of allylic alkylation products in high branch selectivity. We also present conditions for the generation of enantioenriched allylic alkylation products in the presence of catalytic copper and a chiral phosphine ligand. With this approach, diverse and complex products with substituted carbon centers can be generated from simple and abundant feedstock chemicals.
Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones
Li, Chunsheng,Li, Meng,Zhong, Wentao,Jin, Yangbin,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 872 - 875 (2019/05/16)
The first examples of palladium-catalyzed allylic C-H oxidative allylation of sulfoxonium ylides to afford the corresponding conjugated dienones with moderate to good yields have been established. The features of this novel conversion include mild reaction conditions, wide substrate scope, and excellent regioselectivity.
Method for preparing allyl compound
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Paragraph 0028-0034, (2019/11/13)
The invention relates to a method for preparing an allyl compound, and the specific steps are as follows: (1) allyl acetate, a halogenated hydrocarbon, magnesium chips, an additive, a catalyst and a ligand are dissolved in a solvent and mixed, and a crude product is obtained after reaction; and (2) after the crude product obtained in the step (1) is subjected to separation and purification, the allyl compound is obtained. Compared with the prior art, the preparation method effectively avoids the use of a pre-formed organometallic reagent in a traditional synthetic method, and has the characteristics of convenient operation, easy availability of raw materials, low cost, greenness, environmental friendliness and high yield.
Catalytic Oxidative Trifluoromethoxylation of Allylic C?H Bonds Using a Palladium Catalyst
Qi, Xiaoxu,Chen, Pinhong,Liu, Guosheng
supporting information, p. 9517 - 9521 (2017/08/01)
A catalytic intermolecular allylic C?H trifluoromethoxylation reaction of alkenes has been developed based on the use of a palladium catalyst, CsOCF3 as the trifluoromethoxide source, and benzoquinone as the oxidant. This reaction provides an efficient route for directly accessing allylic trifluoromethoxy derivatives with excellent regioselectivities from terminal alkenes via an allylic C?H bond activation process.
Palladium-catalyzed oxidative allylation of bis[(pinacolato)boryl]methane: Synthesis of homoallylic boronic esters
Li, Chunsheng,Li, Meng,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 66 - 69 (2017/12/27)
A palladium-catalyzed oxidative allylation of bis[(pinacolato)boryl]methane to afford the corresponding homoallylic organoboronic esters with moderate to excellent yields is reported. This novel transformation provides an efficient strategy for the construction of homoallylic organoboronic esters in one step with a broad substrate scope. It is proposed that the palladium-catalyzed oxidative allylic C-H bond activation process may be involved in the catalytic cycle.
Palladium-Catalyzed Regioselective Allylation of Chloromethyl(hetero)arenes with Allyl Pinacolborate
Zhang, Sheng,Ullah, Aziz,Yamamoto, Yoshinori,Bao, Ming
supporting information, p. 2723 - 2728 (2017/08/23)
The palladium-catalyzed regioselective allylation reaction between chloromethyl(hetero)arenes and allyl pinacolborate is reported in this work. Chloromethylarenes smoothly reacted with allyl pinacolborate, producing para-allylated dearomatization products
