23170-95-8Relevant academic research and scientific papers
Copper Catalyzed sp3 C-H Etherification with Acyl Protected Phenols
Salvador, Tolani K.,Arnett, Charles H.,Kundu, Subrata,Sapiezynski, Nicholas G.,Bertke, Jeffery A.,Raghibi Boroujeni, Mahdi,Warren, Timothy H.
supporting information, p. 16580 - 16583 (2017/01/10)
A variety of acyl protected phenols AcOAr participate in sp3 C-H etherification of substrates R-H to give alkyl aryl ethers R-OAr employing tBuOOtBu as oxidant with copper(I) β-diketiminato catalysts [CuI]. Although 1°, 2°, and 3° C-H bonds may be functionalized, selectivity studies reveal a preference for the construction of hindered, 3° C-OAr bonds. Mechanistic studies indicate that β-diketiminato copper(II) phenolates [CuII]-OAr play a key role in this C-O bond forming reaction, formed via transesterification of AcOAr with [CuII]-OtBu intermediates generated upon reaction of [CuI] with tBuOOtBu.
Heterogeneous palladium-catalyzed synthesis of aromatic ethers by solvent-free dehydrogenative aromatization: Mechanism, scope, and limitations under aerobic and non-aerobic conditions
Sutter, Marc,Lafon, Romain,Raoul, Yann,Metay, Estelle,Lemaire, Marc
supporting information, p. 5902 - 5916 (2013/09/23)
Starting from cyclohexanone derivatives and alcohols, both non-aromatic precursors, aryl ethers could be synthesized in good yields and with good selectivities in the presence of a catalytic amount of Pd/C, in one step, without added solvent, in a reaction vessel open to air. For less reactive substrates, the addition of 1-octene in a closed system under non-aerobic conditions improved the conversion. In addition, the catalyst could be recycled several times with no decrease in the yield of the aryl ether. The process was also used with tetralone derivatives and polyols. Several reactions were performed to propose a mechanism for this transformation. The formation of an enol ether followed by a dehydrogenation reaction seem to be the key steps of this reaction. Aryl ethers were prepared in good yields and with good selectivities in a solvent-free and heterogeneous catalytic dehydrogenative alkylation of cyclohexanones with various alcohols. Three different complementary routes were used, and for the first time, non-aerobic, safe conditions could be used. Moreover, the catalyst could be recycled several times with no decrease in the yield of the aryl ether. Copyright
Straightforward heterogeneous palladium catalyzed synthesis of aryl ethers and aryl amines via a solvent free aerobic and non-aerobic dehydrogenative arylation
Sutter, Marc,Sotto, Nicolas,Raoul, Yann,Metay, Estelle,Lemaire, Marc
supporting information, p. 347 - 352 (2013/03/28)
Aryl ethers have been prepared from cyclohexanone derivatives and various alcohols in the presence of a catalytic amount of palladium on charcoal. The formation of an enol ether followed by an aerobic or non-aerobic dehydrogenation reaction, seem to be the key steps of this transformation. In addition, this new method was also adapted for the synthesis of arylamines.
ORTHO-ALKYLATION OF PHENOL WITH 2-HEXENE AND 2-OCTENE IN THE PRESENCE OF ALUMINUM PHENOLATE
Kozlikovskii, Ya. B.,Koshchii, V. A.,Ovsiyuk, T. F.
, p. 49 - 54 (2007/10/02)
The alkylation of phenol with 2-hexene and 2-octene in the presence of aluminum phenolate leads to a mixture of corresponding 3- and 2-alkyl phenyl ethers 2-(3-alkyl)-, 2-(2-alkyl)-, and 4-(2-alkyl)phenols, 2-(2-alkyl)-6-(3-alkyl)phenols, and 2,6-di(2-alkyl)phenols.The overall yield of the products from ortho-alkylation amounts to 90-95percent, and the ortho-para ratio is larger than 14:1.
