10540-41-7Relevant academic research and scientific papers
Palladium-catalyzed aerobic dehydrogenation of substituted cyclohexanones to phenols
Izawa, Yusuke,Pun, Doris,Stahl, Shannon S.
, p. 209 - 213 (2011)
Aromatic molecules are key constituents of many pharmaceuticals, electronic materials, and commodity plastics. The utility of these molecules directly reflects the identity and pattern of substituents on the aromatic ring. Here, we report a palladium(II) catalyst system, incorporating an unconventional ortho-dimethylaminopyridine ligand, for the conversion of substituted cyclohexanones to the corresponding phenols. The reaction proceeds via successive dehydrogenation of two saturated carbon-carbon bonds of the six-membered ring and uses molecular oxygen as the hydrogen acceptor. This reactivity demonstrates a versatile and efficient strategy for the synthesis of substituted aromatic molecules with fundamentally different selectivity constraints from the numerous known synthetic methods that rely on substitution of a preexisting aromatic ring.
FLUORINE-CONTAINING COMPOUND AND ANTI-CANCER MEDICAL USE THEREOF
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Paragraph 0071; 0146-0147, (2022/04/03)
The present invention provides a fluorine-containing compound shown in Formula II/III and its anti-cancer medical use.
Photocatalyzed Transition-Metal-Free Oxidative Cross-Coupling Reactions of Tetraorganoborates**
Music, Arif,Baumann, Andreas N.,Boser, Florian,Müller, Nicolas,Matz, Florian,Jagau, Thomas C.,Didier, Dorian
supporting information, p. 4322 - 4326 (2021/02/11)
Readily accessible tetraorganoborate salts undergo selective coupling reactions under blue light irradiation in the presence of catalytic amounts of transition-metal-free acridinium photocatalysts to furnish unsymmetrical biaryls, heterobiaryls and arylated olefins. This represents an interesting conceptual approach to forge C?C bonds between aryl, heteroaryl and alkenyl groups under smooth photochemical conditions. Computational studies were conducted to investigate the mechanism of the transformation.
Lewis acid-promoted site-selective cyanation of phenols
Yang, Wen,Zhang, Wu,Zhao, Wanxiang
supporting information, p. 4604 - 4609 (2020/07/04)
An efficient Lewis acid-promoted site-selective electrophilic cyanation of 3-substituted and 3,4-disubstituted phenols has been developed. The cyanation reactions using MeSCN as the cyanating reagent proceeded efficiently to afford a wide range of 2-hydroxybenzonitriles with high efficiency and excellent regioselectivity. This protocol could provide a practical method for the synthesis and modification of biologically active molecules.
Pd-catalyzed protecting-group-free cross-couplings of iodophenols with atom-economic triarylbismuth reagents
Rao, Maddali L.N.,Meka, Suresh
, (2019/12/30)
An efficient protocol for the protecting-group-free synthesis of unsymmetrical hydroxybiaryls via the Pd-catalyzed cross-couplings of unprotected iodophenols with triarylbismuth reagents is described. The presented protocols exhibits good to high yields of hydroxybiaryls.
Preparation Method for Meta-Substituted Phenol by Oxidative Heck/Dehydrogenation in Microchannel
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Paragraph 0046; 0048-0051; 0056, (2017/05/02)
The present invention relates to a method for efficiently carrying out oxidative Heck/dehydrogenation, which, otherwise, is difficult to be applied to actual production due to an excessively slow reaction rate, although it is useful for preparing a meta-substituted phenol. More particularly, the method for preparing a phenol derivative having a substituent at the meta-position from cyclohexanone through oxidative Heck/dehydrogenation comprises the steps of: (A) introducing cyclohexanone, a boric acid derivative, palladium catalyst and oxygen to a microchannel having a width of 0.1-4.0 mm and carrying out a reaction; (B) further adding tetrafluoroacetic acid (TFA) to the microchannel having a width of 0.1-4.0 mm and including the reaction mixture, while supplying oxygen continuously thereto, and continuously carrying out a reaction.
A Domino Oxidation/Arylation/Protodecarboxylation Reaction of Salicylaldehydes: Expanded Access to meta-Arylphenols
Luo, Junfei,Preciado, Sara,Araromi, Solomon Olatokunbo,Larrosa, Igor
supporting information, p. 347 - 350 (2016/05/19)
A method that allows salicylaldehydes to be efficiently transformed into meta-arylated phenol derivatives through a cascade oxidation/arylation/protodecarboxylation sequence is presented. We demonstrate that the aldehyde functional group can be used as a convenient removable directing group to control site selectivity in C-H activation. Aldehydes are easily introduced into the starting materials and the group is readily cleaved after the C-H functionalization event.
Salicylic acids as readily available starting materials for the synthesis of meta-substituted biaryls
Luo, Junfei,Preciado, Sara,Larrosa, Igor
supporting information, p. 3127 - 3130 (2015/04/14)
Salicylic acids are shown to be readily available and versatile starting materials that easily undergo a tandem arylation-protodecarboxylation process under Pd-catalysis. The corresponding meta-arylphenols can subsequently be easily transformed into a variety of meta-functionalized biaryls, highlighting the versatility of this approach to access this structural motif.
Salicylic acids as readily available starting materials for the synthesis of meta-substituted biaryls
Luo, Junfei,Preciado, Sara,Larrosa, Igor
supporting information, p. 3127 - 3130 (2015/06/03)
Salicylic acids are shown to be readily available and versatile starting materials that easily undergo a tandem arylation-protodecarboxylation process under Pd-catalysis. The corresponding meta-arylphenols can subsequently be easily transformed into a var
Continuous-Flow Synthesis of meta-Substituted Phenol Derivatives
Park, Jeong Hyeon,Park, Chan Yi,Kim, Mi Jin,Kim, Min Uk,Kim, Young Joon,Kim, Geon-Hee,Park, Chan Pil
, p. 812 - 818 (2015/07/27)
Two complementary microreactor technologies were developed for the study of biphasic gas-liquid reactions and preparation of meta-substituted phenol derivatives. The first capillary microreactor, composed of a T-junction and simple capillary, enabled oxidative Heck/dehydrogenation on a microgram scale with a shortened reaction time; the total sequence time for oxidative Heck/dehydrogenation reactions was optimized from 2160 min in a traditional batch system to 130 min in the microchemical system. The second tube-in-tube microreactor, composed of a gas-permeable inner tube and gas-nonpermeable outer tube, successfully performed a gram-scale synthesis under the optimized safety and economic conditions which were established from the first microgram-scale study. The two microreactors have great potential for exploring reactions involving gaseous and liquid reagents.
