881376-69-8Relevant articles and documents
Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water
Li, Tiejun,Peng, Henian,Tang, Wenjun,Tian, Duanshuai,Xu, Guangqing,Yang, He
, p. 4327 - 4337 (2021/05/31)
A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is
1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones
Baschieri, Andrea,Amorati, Riccardo,Valgimigli, Luca,Sambri, Letizia
, p. 13655 - 13664 (2019/10/28)
Pro-aromatic and volatile 1-methyl-1,4-cyclohexadiene (MeCHD) was used for the first time as a valid H-atom source in an innovative method to reduce ortho or para quinones to obtain the corresponding catechols and hydroquinones in good to excellent yields. Notably, the excess of MeCHD and the toluene formed as the oxidation product can be easily removed by evaporation. In some cases, trifluoroacetic acid as a catalyst was added to obtain the desired products. The reaction proceeds in air and under mild conditions, without metal catalysts and sulfur derivatives, resulting in an excellent and competitive method to reduce quinones. The mechanism is attributed to a radical reaction triggered by a hydrogen atom transfer from MeCHD to quinones, or, in the presence of trifluoroacetic acid, to a hydride transfer process.
Electron transfer in complexes of BII cations with organic π-acceptors: A combined experimental and quantum-chemical study
Vogler, Daniel,Wolf, Nina,Kaifer, Elisabeth,Himmel, Hans-J?rg
supporting information, p. 14354 - 14366 (2019/10/11)
Due to their combined Lewis acidity and electron-donor capability, BII cations exhibit an interesting reactivity, which is almost unexplored so far. In this work, we compare the reduction in a dicationic diborane of a series of vicinal diones with different redox potentials, namely 3,5-di-tert-butylbenzoquinone, 3,4,5,6-tetrachlorobenzoquinone, 1,2-naphthalene-dione, 9,10-phenanthrene-dione, 2,2′-dichlorobenzil, benzil and 1,2-acenaphthylene-dione. The experimental work is complemented by quantum-chemical calculations, illuminating the electron-transfer step in the reactions.
