66197-69-1Relevant academic research and scientific papers
Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents
Sousa E Silva, Felipe Cesar,Van, Nguyen T.,Wengryniuk, Sarah E.
supporting information, p. 64 - 69 (2020/01/22)
α-Arylation of α,β-unsaturated ketones constitutes a powerful synthetic transformation. It is most commonly achieved via cross-coupling of α-haloenones, but this stepwise strategy requires prefunctionalized substrates and expensive catalysts. Direct enone C-H α-arylation would offer an atom- and step-economical alternative, but such reports are scarce. Herein we report the metal-free direct C-H arylation of enones mediated by hypervalent iodine reagents. The reaction proceeds via a reductive iodonium Claisen rearrangement of in situ-generated β-pyridinium silyl enol ethers. The aryl groups are derived from ArI(O2CCF3)2 reagents, which are readily accessed from the parent iodoarenes. The reaction is tolerant of a wide range of substitution patterns, and the incorporated arenes maintain the valuable iodine functional handle. Mechanistic investigations implicate arylation via an umpoled "enolonium" species and show that the presence of a β-pyridinium moiety is critical for the desired C-C bond formation.
OXIDATIVE ACETOXYLATION OF THE SILYL ETHERS OF KETONE ENOLS
Brunovlenskaya, I. I.,Kusainova, K. M.,Kashin, A. K.
, p. 316 - 320 (2007/10/02)
The reaction of (diacetoxyiodo)benzene with the trimethylsilyl ethers of ketone enols takes place with retention of the (CH3)3Si group in two directions, i.e., substitution of the vinylic hydrogen or diacetoxylation of the double bond.The reaction can be
Reaction of Enol Silyl Ethers with Silver Carboxylate-Iodine. Synthesis of α-Acyloxy Carbonyl Compounds
Rubottom, George M.,Mott, Robert C.,Juve, Henrik D.
, p. 2717 - 2721 (2007/10/02)
The sequential treatment of enol silyl ethers with silver carboxylate-iodine (2:1) and then fluoride affords high yields of the corresponding α-acyloxy carbonyl compounds.Thus a wide range of variation is now possible for the acyloxy portion of the molecu
