116262-76-1Relevant articles and documents
Room temperature-stable electride as a synthetic organic reagent: Application to pinacol coupling reaction in aqueous media
Buchammagari, Haritha,Toda, Yoshitake,Hirano, Masahiro,Hosono, Hideo,Takeuchi, Daisuke,Osakada, Kohtaro
, p. 4287 - 4289 (2007)
Room temperature-stable inorganic electride [Ca24Al 28O68M]4+4e- was employed for a pinacol coupling reaction in aqueous media. Ca - Al - O gel formed by the destruction of the crystal structure of an electride by water media played a key role in transferring the electron to electrophilic aldehydes. Aromatic aldehydes reacted smoothly with moderate to high yields.
Water accelerated Sm/TMSCl reduction system: Pinacolic coupling of aromatic carbonyl compounds and reductive dimerization cyclization of 1,1- dicyanoalkenes
Wang, Lei,Zhang, Yongmin
, p. 11129 - 11140 (1998)
By action of Sm/TMSCl in THF at room temperature, aromatic carbonyl compounds produce the corresponding 1,2-diols via reductive coupling reaction and 1,1-dicyanoalkenes produce the functionalized cyclopentenes through reductive dimerization followed by intramolecular cyclization in one-pot. The former gives approximately equal amounts of (dl)- and (meso)-1,2-diols and the later gives the major trans-form products. Added micro amounts of water to the system not only can accelerate the reaction, but also increase the yields of products. Moreover, only substoichiometric quantities of metallic samarium are employed.
Novel synthesis of pinacols and sulfones promoted by Smi￡ NiCl2 bimetallic system
Ye, Yuyuan,Zhou, Qizhong,Zheng, Renhua,Jiang, Huajiang,Chen, Rener,Zhang, Yongmin
, p. 331 - 334 (2011)
Smi￡NiCl2 as a reductive system promoted reductive coupling of aryl adehydes and aryl ketone into pinacols in good yields and also promoted coupling reaction of aryl sulfonyl chlorides and active halides into sulfones in good yields.
The scalable pinacol coupling reaction utilizing the inorganic electride [Ca2N]+·e- as an electron donor
Kim, Ye Ji,Kim, Sun Min,Hosono, Hideo,Yang, Jung Woon,Kim, Sung Wng
, p. 4791 - 4794 (2014)
The scalable pinacol coupling reaction is realized utilizing the inorganic electride [Ca2N]+·e- as an electron donor in organic solvents. The bond cleavages of the [Ca2N] + layers by methanol play a vital role in transferring anionic electrons to electrophilic aldehydes, accompanying the formation of Ca(OMe) 2 and ammonia. The Royal Society of Chemistry 2014.
Tellurium-koh mediated rapid pinacolization of carbonyl compounds
Khan, Rahat H.,Mathur, Raj K.,Ghosh, Anil C.
, p. 2193 - 2196 (1997)
A rapid and convenient method is reported for the quantitative pinacolization of aromatic carbonyl compounds with tellurium powder and potassium hydroxide in methanol at ambient temperature.
Rapid Pinacolization of Carbonyl Compounds with Aluminium-KOH
Khurana, Jitender M.,Sehgal, Arti
, p. 571 - 572 (1994)
A rapid and convenient method is reported for the quantitative pinacolization of aromatic carbonyl compounds with aluminium powder and potassium hydroxide in methanol at ambient temperature.
Convenient preparation and reaction of a divalent ytterbium thiolate
Taniguchi, Yuki,Nagata, Kensuke,Kitamura, Tsugio,Fujiwara, Yuzo,Deguchi, Daisuke,Maruo, Masafumi,Makioka, Yoshikazu,Takaki, Ken
, p. 3465 - 3466 (1996)
Ytterbium metal (Yb) reacts with phenylthiotrimethylsilane to generate ytterbium(II) phenylthiolate. The divalent ytterbium thiolate [Yb(SPh)2], thus formed in situ, reacts with aromatic aldehydes to give pinacols.
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)
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.
Reductive Coupling of Aromatic Carbonyl Compounds to Pinacols Using Zinc Powder in Aqueous Media
Wang, Lei,Sun, Xinghua,Zhang, Yongmin
, p. 336 - 337 (1998)
Zinc-mediated reductive coupling of aromatic carbonyl compounds occurs to give corresponding 1,2-diols in moderate to good yields in saturated NH4Cl(aq)-THF solution at room temperature.
A highly diastereoselective pinacol coupling reaction of aldehydes and ketones using low-valence niobium generated from Nb(V)
Arai, Shigeru,Sudo, Yukinori,Nishida, Atsushi
, p. 287 - 288 (2004)
A simple method for the diastereoselective synthesis of racemic 1,2-diol mediated by low-valence niobium generated in situ is described. A 1,4-dioxane-toluene solvent system was found to be essential to achieve higher selectivities and to prevent other reactions of pinacols, such as deoxygenation and acetal formation. Aromatic aldehydes and ketones were converted to the corresponding pinacols with up to 97 and 85% de, respectively.
