1636-34-6Relevant articles and documents
Mc Bay
, p. 1883,1886 (1975)
Intramolecular and intermolecular ketone-ester reductive coupling reactions promoted by samarium(II) iodide
Liu, Yunkui,Zhang, Yongmin
, p. 5745 - 5748 (2001)
Intramolecular and intermolecular ketone-ester reductive coupling reactions promoted by SmI2 have been studied. Substituted 2-hydroxy-5-ethoxycarbonylcyclopentanones, 5-ethoxycarbonylcyclopentenones and α-ketols were prepared in moderate to good yields at room temperature or under reflux under neutral conditions.
Conway et al.
, p. 87,90, 96 (1968)
A Simple and Efficient New Synthesis of Vicinal Diols by Reductive Coupling of Carbonyl Compounds
Csuk, Rene,Fuerstner, Alois,Weidmann, Hans
, p. 1802 - 1803 (1986)
A universally applicable, new 'pinacolic reduction' for aldehydes and ketones is described.
Domrachev et al.
, (1978)
Cram,Wilson
, p. 1245 (1963)
Radical pairs with rotational fluidity in the photochemical reaction of acetophenone and cyclohexane in the zeolite NAY: A 13C CPMAS NMR and product analysis study
Amboya, Ammee,Nguyen, Tina,Huynh, Hien T.,Brown, Ashley,Ratliff, Gretchen,Yonutas, Heather,Cizmeciyan, Deniz,Natarajan, Arunkumar,Garcia Garibay, Miguel A.
, p. 2322 - 2326 (2009)
The photochemical reaction of acetophenone and cyclohexane in the zeolite NaY occurs by combination of the geminate radical pairs to give products that reveal a significant amount of rotational fluidity, which was also documented by intermolecular nuclear dipolar interaction measurements using cross polarization 13C NMR (CPMAS) experiments. The Royal Society of Chemistry 2009.
Agahigian et al.
, p. 194 (1963)
Diastereoselective pinacol coupling of alkyl aryl ketones with rare earth metals in the presence of chlorosilanes
Ogawa, Akiya,Takeuchi, Hiroki,Hirao, Toshikazu
, p. 7113 - 7114 (1999)
Rare earth metals (Ln) are found to act as useful reducing agents for the pinacol coupling reaction of alkyl aryl ketones in the presence of chlorosilanes. Although the hitherto known pinacol coupling reaction using rare earth reducing agents generally exhibits very low diastereoselectivities, the present pinacol coupling by use of a Ln/R3SiCl system usually indicates higher diastereoselectivities. In particular, a Yb/Me3SiCl system attains the diastereoselective pinacol coupling of primary alkyl aryl ketones with the dl/meso ratio of 8/2~9/1.
Horner,Degner
, p. 5889 (1968)
A convenient pinacol coupling of diaryl ketones with B2pin2viapyridine catalysis
Jo, Junhyuk,Kim, Seonyul,Choi, Jun-Ho,Chung, Won-Jin
supporting information, p. 1360 - 1363 (2021/02/22)
A convenient, pyridine-boryl radical-mediated pinacol coupling of diaryl ketones is developed. In contrast to the conventional pinacol coupling that requires sensitive reducing metal, the current method employs a stable diboron reagent and pyridine Lewis base catalyst for the generation of a ketyl radical. The newly developed process is operationally simple, and the desired diols are produced with excellent efficiency in up to 99% yield within 1 hour. The superior reactivity of diaryl ketone was observed over monoaryl carbonyl compounds and analyzed by DFT calculations, which suggests the necessity of both aromatic rings for the maximum stabilization of the transition states.
Luminescent tungsten(vi) complexes as photocatalysts for light-driven C-C and C-B bond formation reactions
Chan, Kaai-Tung,Che, Chi-Ming,Du, Lili,Liu, Yungen,Phillips, David Lee,To, Wai-Pong,Tong, Glenna So Ming,Wu, Liang-Liang,Yu, Daohong
, p. 6370 - 6382 (2020/07/15)
The realization of photocatalysis for practical synthetic application hinges on the development of inexpensive photocatalysts which can be prepared on a large scale. Herein an air-stable, visible-light-absorbing photoluminescent tungsten(vi) complex which can be conveniently prepared at the gram-scale is described. This complex could catalyse photochemical organic transformation reactions including borylation of aryl halides, such as aryl chloride, reductive coupling of benzyl bromides for C-C bond formation, reductive coupling of phenacyl bromides, and decarboxylative coupling of redox-active esters of alkyl carboxylic acid with high product yields and broad functional group tolerance.
How the sustainable solvent water unleashes the photoredox catalytic potential of ruthenium polypyridyl complexes for pinacol couplings
Naumann, Robert,Goez, Martin
, p. 4470 - 4474 (2019/08/21)
By complementing laser flash photolysis with product studies in visible-LED driven syntheses, we show that the one-electron reduced forms OER of tris(2,2′-bipyridine)ruthenium(ii) and its more reactive derivative with 4,4′-dimethylated ligands exhibit a reductive power greater by 0.2 eV in water than in acetonitrile; and that this difference allows the reduction of carbonyl compounds, and thus pinacol couplings, in aqueous medium via ruthenium-based photoredox catalysis as an alternative to using more expensive and less photostable higher-energy complexes (e.g., of iridium). Ascorbate serves as sacrificial donor to access OER. SDS micelles or cyclodextrins as carriers help overcome solubility problems of less hydrophilic substrates, and more reactive water-soluble substrates can even be coupled at neutral pH, such that the mild conditions make the process fully sustainable.
