46863-20-1Relevant academic research and scientific papers
Acyl radical smiles rearrangement to construct hydroxybenzophenones by photoredox catalysis
Li, Junzhao,Liu, Zhengyi,Wu, Shuang,Chen, Yiyun
supporting information, p. 2077 - 2080 (2019/03/29)
The first visible-light-induced acyl radical Smiles rearrangement to transform biaryl ethers to hydroxybenzophenones under mild and metal-free conditions is reported. Using the dual catalysis of hypervalent iodine(III) reagents and organophotocatalysts, ketoacids readily generate acyl radicals and undergo 1,5-ipso addition. This method can construct electron-deficient and electron-rich hydroxybenzophenones with excellent chemoselectivity and on gram scale. The performance of the reaction in neutral aqueous conditions holds potential for future biomolecule applications.
Synthesis of ortho-acylphenols through the palladium-catalyzed ketone-directed hydroxylation of arenes
Mo, Fanyang,Trzepkowski, Louis J.,Dong, Guangbin
supporting information, p. 13075 - 13079 (2013/02/25)
ortho-Acylphenols are an important structural motif found in a diversity of bioactive molecules ranging from natural products to drugs (Figure 1). Moreover, they also serve as versatile building blocks for the synthesis of various pharmaceuticals, such as warfarin, as well as agrichemicals, flavors, and fragrances. Classic approaches to the synthesis of o-acylphenols generally involve a two-step process: acylation of phenols followed by Fries rearrangement of the resulting phenyl esters (Scheme 1a). On the other hand, direct C-acylation of phenols has also been known under more forcing conditions. Although effective, these approaches are often complicated by the formation of undesired p-substituted products when bulky acyl groups need to be introduced, as well as the limited variety of ketones that can be generated.
A concise approach to the preparation of 2-hydroxydiarylketones by an intramolecular acyl radical ipso substitution
Motherwell,Vazquez
, p. 9667 - 9671 (2007/10/03)
Substituted 2-hydroxydiarylketones have been simply prepared using an intramolecular acyl radical [1,6] ipso substitution reaction. (C) 2000 Elsevier Science Ltd.
Modification of Photochemical Reactivity by Cyclodextrin Complexation: Product Selectivity in Photo-Fries Rearrangement
Syamala, M. S.,Rao, B. Nageswer,Ramamurthy, V.
, p. 7234 - 7242 (2007/10/02)
Cyclodextrin encapsulation, both in the solid state and in aqueous solution brings about a remarkable regulation of the photo-Fries rearrangement of phenyl esters and anilides.In comparison to the non-selective mixture of ortho and para-rearranged isomers along with the deacylated product obtained in organic solvents, the solid β-cyclodextrin complexes of unsubstituted esters and anilides show a remarkable 'ortho-selectivity'.An impressive 'regio-selectivity' among the two ortho-rearranged isomers is observed for meta-substituted esters and anilides upon irradiation as β-cyclodextrin complexes.Specific orientations of the unsubstituted and meta-substituted esters and anilides in the β-cyclodextrin cavity are suggested to be responsible for the observed selectivity.
