1070-83-3Relevant articles and documents
CATALYTIC OXIDATION OF ALDEHYDES TO CARBOXYLIC ACIDS WITH HYDROGEN PEROXYDE AS OXIDANT
Choi, Joong-Kwon,Chang, Young-Kil,Hong, Sung Yeap
, p. 1967 - 1970 (1988)
Alkyl and aryl aldehydes were catalytically oxidized to carboxylic acids in high yields with hydrogen peroxide as oxidant using benseneseleninic acid as catalyst.
Correlation of rates of uncatalyzed and hydroxide-ion catalyzed ketene hydration. A mechanistic application and solvent isotope effects on the uncatalyzed reaction
Andraos, John,Kresge, A. Jerry
, p. 508 - 515 (2000)
Rates of hydration of a number of ketenes were measured in neutral and basic solution using flash photolytic techniques, and rate constants for their uncatalyzed, k(uc), and hydroxide-ion catalyzed, k(HO), reactions were determined. These results, plus additional data from the literature, were found to provide the remarkably good correlation log k(uc) = -3.21 + 1.14 log k(HO), which spans 10 orders of magnitude in reactivity and includes 31 ketenes. This good correlation implies that uncatalyzed and hydroxide-ion catalyzed ketene hydraton occur by similar reaction mechanisms, which for the hydroxide-ion catalyzed process is known to involve nucleophilic attack on the carbonyl carbon atom of the ketene. Rate constants for phenylhydroxyketene, on the other hand, do not fit this correlation, which suggests that the mechanistic assignment upon which these rate constants are based may not be correct. Solvent isotope effects on these uncatalyzed ketene hydrations are weak; most are less than k(H)/k(D) = 2. It is argued that these isotope effects are largely, if not entirely, secondary in nature and that they are consistent with both a reaction mechanism in which nucleophilic attack of a single water molecule on the ketene carbonyl carbon atom produces a zwitterionic intermediate and also a mechanism that avoids this intermediate by passing through a cyclic transition state involving several water molecules.
Novel diastereoselective synthesis of (E)-gem-dimetalloalkenes containing boron and germanium: An easy access to alkyl trimethylgermyl ketones and carboxylic acids
Bhat, Narayan G.,Varghese, Nisha
, p. 2023 - 2024 (2007)
A convenient, novel synthesis of (E)-gem-dimetalloalkenes containing boron and germanium from the (Z)-1-bromo-1-alkenylboronate esters has been developed. α-Bromo-(Z)-1-alkenylboronate esters readily prepared from the literature procedures smoothly underwent a reaction with freshly generated trimethylgermyllithium in hexamethylphosphoramide (HMPA) from the hexamethyldigermanium at -78°C to provide the corresponding 'ate' complexes. These 'ate' complexes underwent intramolecular nucleophilic substitution reaction to provide the corresponding (E)-1-alkenylboronate esters containing trimethylgermyl moiety. These intermediates were isolated in good yields (72-81%) and were characterized by the spectral data (1H NMR and 13C NMR). Upon oxidation of these intermediates with trimethylamine-N-oxide, the corresponding alkyl trimethylgermyl ketones were prepared in good yields (78-86%)). Oxidation with alkaline hydrogen peroxide followed by acidification afforded the corresponding carboxylic acids in good yields (82-88%). Georg Thieme Verlag Stuttgart.
Organoboranes for Synthesis. 14. Convenient Procedures for the Direct Oxidation of Organoboranes from Terminal Alkenes to Carboxylic Acids
Brown, Herbert C.,Kulkarni, Shekhar V.,Khanna, Vijay V.,Patil, Virendra D.,Racherla, Uday S.
, p. 6173 - 6177 (1992)
For the first time, a highly efficient and direct oxidation of a variety of organoborane intermediates into carboxylic acids has been demonstrated, without an increase or decrease of carbon atoms.Synthetically useful procedures have been developed for the ready conversion of representative terminal alkenes into carboxylic acids via oxidation of the organoboranes obtained by hydroboration of the terminal alkenes.The oxidation works well with a variety of organoboranes derived from reagents such as dibromoborane-methyl sulfide (HBBr2*SMe2), monobromoborane-methyl sulfide (H2BBr*SMe2), monochloroboran-methyl sulfide (H2BCl*SMe2), borane-methyl sulfide (H3B*SMe2), thexylborane (H2BThx), and dicyclohexylborane (HBChx2).The oxidation is achieved in a convenient manner with pyridinium dichromate (PDC), sodium dichromate in aqueous sulfuric acid (Na2Cr2O7-H2SO4) and chromium trioxide in 90 percent aqueous acetic acid (CrO3-HOAc-H2O).These oxidations afford carboxylic acids in very good yields with complete retention of the structure of the organic group attached to boron.
Ni(I)-Alkyl Complexes Bearing Phenanthroline Ligands: Experimental Evidence for CO2Insertion at Ni(I) Centers
Hazari, Nilay,Hopmann, Kathrin H.,Martin, Ruben,Obst, Marc F.,Odena, Carlota,Somerville, Rosie J.
, p. 10936 - 10941 (2020)
Although the catalytic carboxylation of unactivated alkyl electrophiles has reached remarkable levels of sophistication, the intermediacy of (phenanthroline)Ni(I)-alkyl species - complexes proposed in numerous Ni-catalyzed reductive cross-coupling reactions - has been subject to speculation. Herein we report the synthesis of such elusive (phenanthroline)Ni(I) species and their reactivity with CO2, allowing us to address a long-standing question related to Ni-catalyzed carboxylation reactions.
A convenient procedure for the direct conversion of terminal alkenes into carboxylic acids
Racherla,Khanna,Brown
, p. 1037 - 1040 (1992)
Alkylboronic acids, readily synthesized from a variety of representative terminal alkenes via hydroboration with dibromoborane-methyl sulfide, undergo a facile oxidation with chromium trioxide in 90% aqueous acetic acid to provide carboxylic acids in 80-97% isolated yields, without rearrangement or loss of carbon.
Preparation method of bimetallic catalyst oxidation aldehyde synthetic carboxylic acid (by machine translation)
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Paragraph 0046-0047, (2020/05/30)
The method is, in a reaction solvent: under normal pressure oxygen condition, under the action of a bimetallic catalyst under the action of a bimetallic catalyst under the action of a bimetallic catalyst under the action of a bimetallic catalyst, at, DEG, under stirring . under a stirring condition with an aldehyde compound as a substrate 10-90 °C in a reaction solvent under, a stirring condition under the action of a bimetallic catalyst . The reaction solution is stirred, for. 1-12h, hours at; room temperature, under, the action, of a bimetallic 1:1 catalyst Cu(OAc) under the action of a bimetallic catalyst under the action of a bimetallic catalyst under the action of a double-metal catalyst. 2 · H2 O And Co(OAc)2 · 44H2 O As the bimetallic catalyst, can achieve the highest yield of the carboxylic acid product, in high yield, by adjusting the reaction temperature, solvent, catalyst amount, for different types of the raw material aldehyde 98%. (by machine translation)
Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides
Li, Chenchen,Li, Ruoling,Zhang, Bing,Zhao, Pei,Zhao, Wanxiang
supporting information, p. 10913 - 10917 (2020/05/25)
A general efficient protocol was developed for the synthesis of carboxylic acids, esters, and amides through oxidation of alkynyl boronates, generated directly from terminal alkynes. This protocol represents the first example of C(sp)?B bond oxidation. This approach displays a broad substrate scope, including aryl and alkyl alkynes, and exhibits excellent functional group tolerance. Water, primary and secondary alcohols, and amines are suitable nucleophiles for this transformation. Notably, amino acids and peptides can be used as nucleophiles, providing an efficient method for the synthesis and modification of peptides. The practicability of this methodology was further highlighted by the preparation of pharmaceutical molecules.
Organocatalyzed Aerobic Oxidation of Aldehydes to Acids
Dai, Peng-Fei,Qu, Jian-Ping,Kang, Yan-Biao
supporting information, p. 1393 - 1396 (2019/02/26)
The first example organocatalyzed aerobic oxidation of aldehydes to carboxylic acids in both organic solvent and water under mild conditions is developed. As low as 5 mol % N-hydroxyphthalimide was used as the organocatalyst, and molecular O2 was used as the sole oxidant. No transition metals or hazardous oxidants or cocatalysts were involved. A wide range of carboxylic acids bearing diverse functional groups were obtained from aldehydes, even from alcohols, in high yields.
A aldehyde or mellow directly converted into the carboxylic acid (by machine translation)
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Paragraph 0031; 0032, (2018/08/03)
The invention discloses a aldehyde or mellow oxidation can be directly transformed into carboxylic acid, is characterized in that the pure oxygen environment, in N - hydroxy imide compound under the catalysis of the imide compound or N - hydroxy and nitrous acid ester compound common under the catalysis, the CH2 OH and CHO oxidation directly converted into the carboxylic acid compounds. The invention using oxygen as the oxidizing agent, does not add any metal catalyst, environment-friendly, high catalytic efficiency, simple and convenient operation. With the previous metal catalytic system complex and different catalytic system, has some metal catalytic system in the process, the use of transition metal will cause the transition metal of the residual, the invention adopts the non-metallic catalytic system, environmental protection, preventing the metal residue problem, this to the solution of the drug in the synthesis of transition metal residue problem and provides a new method of thinking. (by machine translation)
