53780-43-1Relevant academic research and scientific papers
Silver(I)-catalyzed reaction between pyrazole and propargyl acetates: Stereoselective synthesis of the scorpionate ligands (E)-allyl-gem-dipyrazoles (ADPs)
Bhanuchandra,Kuram, Malleswara Rao,Sahoo, Akhila K.
, p. 11824 - 11834 (2014/01/06)
The reaction between readily accessible pyrazole and propargyl acetates in the presence of Ag(I) catalyst yielded a new class of (E)-allyl-gem-dipyrazole scorpionate ligands: 1-aryl-2-N-pyrazolyl allyl acetates and 1,3-dipyrazolyl-3-arylpropene. The reaction showed broad substrate scope, and various functional and protecting groups were tolerated under the reaction conditions. The palladium(II) scorpionate complex could thus be easily prepared and successfully employed in Suzuki-Miyaura cross-couplings in water.
Gold-catalyzed regioselective hydration of propargyl acetates assisted by a neighboring carbonyl group: Access to α-acyloxy methyl ketones and synthesis of (±)-actinopolymorphol B
Ghosh, Nayan,Nayak, Sanatan,Sahoo, Akhila K.
, p. 500 - 511 (2011/04/17)
A general atom-economical approach for the synthesis of α-acyloxy methyl ketone is demonstrated through regioselective hydration of a wide range of propargyl acetates. Readily available catalyst comprising of 1% Ph 3PAuCl and 1% AgSbF6 in dioxane-H2O efficiently hydrolyzes the terminal alkynes of the propargyl acetate in the absence of acid promoters at ambient temperature within a short time. Effective regioselective hydration is facilitated by the neighboring carbonyl group as demonstrated through 18O-labeling study. Compatibility of functional moieties and tolerance to various acid-labile protecting groups are observed. The catalytic condition is also suitable to perform hydration of TMS-substituted propargyl acetates, even though it requires prolonged reaction time for completion. Stereointegrity of the propargylic acetate is preserved during the hydration. The robustness of the system is successfully demonstrated through gram scale preparation of the product in nearly quantitative yield. The common α-acyloxy methyl ketone is transformed to 1,2-diol and 1,2-amino alcohol derivatives. Synthesis of actinopolymorphol B is achieved for the first time involving hydration of the propargyl acetate as the key step.
Synthesis of Non-Ester Pyrethroids Having a 1-Fluoro-1-methylethyl Group Using 1,2-Migration of an Aryl Group
Uneme, Hideki,Okada, Yoshiyuki
, p. 2401 - 2410 (2007/10/02)
When 1,4-diaryl-4-methyl-1,3-pentanediol was treated with diethylaminosulfur trifluoride to introduce fluorine atoms into the central link, 1,2-aryl group migration products which have a 1-fluoro-1-methylethyl group were obtained as two diastereomers.Util
Preparation of Optically Active Secondary Alcohols Related to Synthetic Pyrethroids by Microbial Asymmetric Hydrolysis of the Corresponding Acetates
Sugai, Takeshi,Kuwahara, Shigefumi,Hoshino, Chimaki,Matsuo, Noritada,Mori, Kenji
, p. 2579 - 2586 (2007/10/02)
Asymmetric hydrolysis of the acetates of racemic secondary alcohols related to synthetic pyrethroids by Bacillus subtilis var. niger (IFO 3108) yielded optically active acetates and alcohols of varying optical purities.
M-phenoxybenzyl and α-cyano-M-phenoxybenzyl esters of 2-haloalkyl (oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids
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, (2008/06/13)
The invention is m-phenoxybenzyl esters of 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful insecticidal and acaricidal agents.
