13811-19-3Relevant academic research and scientific papers
Fluoride anion-initiated bis-trifluoromethylation of phenyl aromatic carboxylates with (trifluoromethyl)trimethylsilane
Takahashi, Kenjiro,Ano, Yusuke,Chatani, Naoto
supporting information, p. 11661 - 11664 (2020/10/19)
The fluoride anion-initiated reaction of phenyl aromatic carboxylates with (trifluoromethyl)trimethylsilane (Me3SiCF3) that results in the formation of O-silyl-protected 2-aryl-1,1,1,3,3,3-hexafluoroisopropanols is reported. A phenoxide anion, generated during the trifluoromethylation of the phenyl carboxylate, also activates the Me3SiCF3, which permits a catalytic amount of the fluoride anion source to be used. Various functional groups, which can be used for further elaboration, are tolerated in the reaction.
Ligand-Controlled C?O Bond Coupling of Carboxylic Acids and Aryl Iodides: Experimental and Computational Insights
Li, Li,Song, Feifei,Zhong, Xiumei,Wu, Yun-Dong,Zhang, Xinhao,Chen, Jiean,Huang, Yong
supporting information, p. 126 - 132 (2019/11/28)
Palladium-catalyzed cross-coupling reactions between carboxylic acids and aryl halides have several possible competitive pathways. Decarboxylative C?C bond coupling and C?H arylation are well established in the literature. However, direct C?O bond coupling between carboxylic acids and aryl halides has received little success. In this report, we describe a protocol for exclusive C?O bond formation, enabled by a bidentate N,N-ligand such as 1,10-phenanthroline. The reaction is general for a broad range of carboxylic acids and iodoarenes. Experimental evidence and computational results suggest a high energy barrier for the alternative pathway of decarboxylative carbon-carbon bond coupling. (Figure presented.).
Palladium-catalyzed carbonylation of aryl, alkenyl, and allyl halides with phenyl formate
Ueda, Tsuyoshi,Konishi, Hideyuki,Manabe, Kei
supporting information; experimental part, p. 3100 - 3103 (2012/07/27)
Highly efficient palladium-catalyzed carbonylation of aryl, alkenyl, and allyl halides with phenyl formate is reported. This procedure does not use carbon monoxide and affords one-carbon-elongated carboxylic acid phenyl esters in excellent yields. The reaction proceeds smoothly under mild conditions and tolerates a wide range of functional groups including aldehyde, ether, ketone, ester, and cyano groups. Furthermore, a variety of heteroaromatic bromides can be converted to the corresponding phenyl esters in high yields.
