- Synthesis of Ketones through Microwave Irradiation Promoted Metal-Free Alkylation of Aldehydes by Activation of C(sp3)-H Bond
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In this paper, a novel methodology for the synthesis of ketones via microwave irradiation promoted direct alkylation of aldehydes by activation of the inert C(sp3)-H bond has been developed. Notably, the reactions were accomplished under metal-free conditions and used commercially available aldehydes and cycloalkanes as substrates without prefunctionalization. By using this novel method, an alternative synthetic approach toward the key intermediates for the preparation of the pharmaceutically valuable oxaspiroketone derivatives was successfully established.
- Zhang, Xinying,Wang, Zhangxin,Fan, Xuesen,Wang, Jianji
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p. 10660 - 10667
(2015/11/18)
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- The insertion of arynes into the O-H bond of aliphatic carboxylic acids
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The insertion of arynes into the O-H bond of aliphatic carboxylic acids promoted by sodium carboxylates is described. The reactions led to the formation of aryl carboxylates in good yields with good chemoselectivities under mild conditions.
- Wen, Chunxiao,Chen, Qian,He, Zhenwen,Yan, Xinxing,Zhang, Changyuan,Du, Zhiyun,Zhang, Kun
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supporting information
p. 5470 - 5473
(2015/09/15)
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- Intermolecular C-O addition of carboxylic acids to arynes: Synthesis of o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones
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An efficient and simple route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed utilizing readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl tr
- Dubrovskiy, Anton V.,Larock, Richard C.
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p. 2789 - 2798
(2013/03/29)
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- Intermolecular C-O addition of carboxylic acids to arynes
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(Figure Presented) A novel, efficient, and expedient route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed starting from readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl triflates.
- Dubrovskiy, Anton V.,Larock, Richard C.
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supporting information; experimental part
p. 3117 - 3119
(2010/08/22)
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- Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions: Synthetic and Mechanistic Insights
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Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 °C. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.
- Coe, Jotham W.,Bianco, Krista E.,Boscoe, Brian P.,Brooks, Paige R.,Cox, Eric D.,Vetelino, Michael G.
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p. 9964 - 9970
(2007/10/03)
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