84839-89-4Relevant academic research and scientific papers
Electrochemical α-Arylation of Ketones via Anodic Oxidation of in Situ Generated Silyl Enol Ethers
Jud, Wolfgang,Sommer, Florian,Kappe, C. Oliver,Cantillo, David
, p. 16026 - 16034 (2021/08/24)
An electrochemical procedure for the α-arylation of ketones has been developed. The method is based on the generation and one-pot anodic oxidation of silyl enol ethers in the presence of the arene. This strategy avoids isolation of the silyl enol intermediate and the utilization of external supporting electrolytes. Intermolecular arylations, which had not been reported so far, are possible when electron-rich arenes are utilized as coupling partners. The method has been demonstrated for a wide variety of aryl ketones and activated arenes, with moderate to good yields (up to 69%) obtained. Mechanistic insights and a theoretical rationale that explains the ketone α-arylation versus dimerization selectivity are also presented.
The Chemistry of Aryllead(IV) Tricarboxylates. Reaction with Silyl Enol Ethers
Bell, Craig H.,Pinhey, John T.,Sternhell, Sever
, p. 2237 - 2245 (2007/10/02)
The trimethylsilyl enol ether of acetophenone (1) and p-methoxyphenyllead triacetate (2) react to give (p-methoxyphenyl)phenacyllead(IV) diacetate (4) in high yield.This plumbation reaction has been studied for a number of ketone trimethylsilyl enol ethers and aryllead triacetates, and it would appear that it is probably limited to aryl ketone trimethylsilyl enol ethers.The trifluoroacetic acid catalysed break down of these α-plumbated ketones to substituted deoxybenzoins has been examined in considerable detail.The thermal decomposition of one of the lead compounds to a deoxybenzoin derivative has also been examined.
