A new arylation of silyl enol ethers by quinone monoacetal substitution

作者：Dohi Toshifumi; Kamitanaka Tohru; Takamuro Hitoho; Mishima Yusuke; Washimi Naohiko; Kita Yasuyuki^*

来源：Tetrahedron Letters, 2015, 56(23): 3046-3051.

DOI：10.1016/j.tetlet.2014.11.085

• Arylation
• Silyl enol ether
• Quinone monoacetal
• Substitution
• alpha-Aryl carbonyl compound

Quinone monoacetals (QMAs) were found to be convenient substrates for a unique arylation reaction of enol silyl ethers. This arylation process of QMAs typically proceeds through the acetal activation of the QMAs by a hydrogen-bond donor solvent, such as a fluoroalcohol, for the initiating step. The silyl transfer from silyl enol ethers to the carbonyl oxygen of the QMAs appears to be involved in the C-C coupling step, followed by QMA aromatization. By this method, valuable alpha-aryl carbonyl compounds containing o-phenol moieties can be obtained directly under mild conditions without lactone formation.

• 出版日期2015-6-3