- Decarboxylative Oxygenation via Photoredox Catalysis
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The direct conversion of aliphatic carboxylic acids to their dehomologated carbonyl analogues has been accomplished through photocatalytic decarboxylative oxygenation. This transformation is applicable to an array of carboxylic acid motifs, producing ketones, aldehydes, and amides in excellent yields. Preliminary results demonstrate that this methodology is further amenable to aldehyde substrates via in situ oxidation to the corresponding acid and subsequent decarboxylative oxygenation. We have exploited this strategy for the sequential oxidative dehomologation of linear aliphatic chains.
- Faraggi, Tomer M.,Li, Wei,MacMillan, David W. C.
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p. 410 - 415
(2019/12/24)
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- Photoredox-Catalyzed Decarboxylative Oxidation of Arylacetic Acids
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A photoredox-catalyzed decarboxylative oxidation of arylacetic acids, which are privileged scaffolds in pharmaceuticals, is reported herein. The established method is operationally simple and a variety of substrates are applicable, providing rapid access to dehomologated bioisosteres of common pharmaceuticals.
- Sakakibara, Yota,Cooper, Phillippa,Murakami, Kei,Itami, Kenichiro
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supporting information
p. 2410 - 2413
(2018/06/04)
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- Chemoenzymatic synthesis of (2S)-2-arylpropanols through a dynamic kinetic resolution of 2-arylpropanals with alcohol dehydrogenases
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We applied Horse Liver Alcohol Dehydrogenase (HLADH) to the enantioselective synthesis of six (2S)-2-arylpropanols, useful intermediates in the synthesis of Profens. The influence of substrate structure and reaction conditions on yields and enantioselectivity were investigated. The high yields and high enantioselectivity towards the (S)-enantiomer obtained in the bioreduction of 2-arylpropionic aldehydes, clearly indicate the achievement of a DKR process through a combination of an enzyme-catalyzed kinetic reduction with a chemical base-catalyzed racemization of the unreacted aldehydes. The racemization step is represented by the keto-enol equilibrium of the aldehyde and can be controlled by modulating pH and reaction conditions.
- Galletti, Paola,Emer, Enrico,Gucciardo, Gabriele,Quintavalla, Arianna,Pori, Matteo,Giacomini, Daria
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experimental part
p. 4117 - 4123
(2010/10/03)
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- One-step oxidation of 2-arylpropanols to 2-arylpropionic acids: Improving sustainability in the synthesis of profens
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Three oxidation procedures were evaluated for the synthesis of optically pure 2-arylpropionic acids. Efficient, mild, and eco-friendly conditions were obtained with the system comprising TEMPO, NaClO, and NaClO2. Thus a series of profens were obtained in good to excellent yields. Georg Thieme Verlag Stuttgart New York.
- Galletti, Paola,Pori, Matteo,Giacomini, Daria
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experimental part
p. 2644 - 2648
(2010/11/18)
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- Oxidative conversion of α,α-disubstituted acetamides to corresponding one-carbon-shorter ketones using hypervalent iodine (λ5) reagents in combination with tetraethylammonium bromide
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(Chemical Equation Presented) α,α-Disubstituted acetamides undergo oxidative dehomologation to give one-carbon-shorter ketones when reacted with a hypervalent iodine (λ5) reagent in combination with tetraethylammonium bromide (TEAB) in various solvents. In further studies, one such combination of a hypervalent iodine (λ5) reagent, o-iodoxybenzoic acid, and TEAB has been established as a new, mild, efficient, and general method for the transformation.
- Bellale, Eknath V.,Bhalerao, Dinesh S.,Akamanchi, Krishnacharya G.
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supporting information; experimental part
p. 9473 - 9475
(2009/04/06)
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- Process for producing biphenyl derivatives
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A process for producing a halobiphenyl derivative represented by the following formula (I) comprises dehydrogenating a cyclohexylhalobenzene represented by the following formula (II) under such conditions that substantially no dehalogenation occurs. STR1 wherein X represents a halogen atom, and each of R1 and R2 independently represents a group represented by the formula STR2 wherein A represents carboxyl or an alkoxycarbonyl group and R represents a hydrogen atom or a lower alkyl group; an alkylcarbonyl; alkenyl; alkynyl; alkyl; aryl; arylcarbonyl; hydroxyalkyl; cyanoalkyl or cyanoalkenyl group.
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- Therapeutically active phenylalkane derivatives
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2-(2-Fluoro-4-biphenylyl)propan-1-ol, 2-(2'-Fluoro-4-biphenylyl)propan-1-ol and 2-(2,2'-Difluoro-4-biphenylyl)propan-1-ol Possessing great anti-inflammatory, analgesic and antipyretic activities.
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