13145-58-9Relevant articles and documents
Stocker et al.
, p. 412 (1968)
A novel, solventless reductive coupling of carbonyl compounds by alkali metals, catalysed by bromobenzene
Zhao, Hui,Li, De-Jin,Deng, Lan,Liu, Lei,Guo, Qing-Xiang
, p. 506 - 507 (2003)
Catalysed by bromobenzene, alkali metals including Li, Na, and K can mediate the reductive coupling of carbonyl compounds under mild, solventless conditions to furnish the corresponding pinacol products.
Lewis Acid Assisted Electrophilic Fluorine-Catalyzed Pinacol Rearrangement of Hydrobenzoin Substrates: One-Pot Synthesis of (±)-Latifine and (±)-Cherylline
Shi, Hui,Du, Chuan,Zhang, Xinhang,Xie, Fukai,Wang, Xiaoyu,Cui, Shanshan,Peng, Xiaoshi,Cheng, Maosheng,Lin, Bin,Liu, Yongxiang
, p. 1312 - 1319 (2018/02/09)
A microwave-irradiated solvent-free pinacol rearrangement of hydrobenzoin substrates catalyzed by a combination of N-fluorobenzenesulfonimide and FeCl3·6H2O was developed. Its selectivity was first investigated by density functional theory (DFT) calculations. Then the functional group tolerance was examined by synthesizing a series of substrates designed based on the insight provided by the DFT calculations. The application of the methodology was demonstrated by the efficient one-pot synthesis of (±)-latifine and (±)-cherylline, both are 4-aryltetrahydroisoquinoline alkaloids isolated from Amaryllidacecae plants.
Homogeneous and heterogeneous photoredoxcatalyzed hydroxymethylation of ketones and keto esters: Catalyst screening, chemoselectivity and dilution effects
Griesbeck, Axel G.,Reckenthaeler, Melissa
supporting information, p. 1143 - 1150 (2014/06/09)
The homogeneous titanium- and dye-catalyzed as well as the heterogeneous semiconductor particle-catalyzed photohydroxymethylation of ketones by methanol were investigated in order to evaluate the most active photocatalyst system. Dialkoxytitanium dichlorides are the most efficient species for chemoselective hydroxymethylation of acetophenone as well as other aromatic and aliphatic ketones. Pinacol coupling is the dominant process for semiconductor catalysis and ketone reduction dominates the Ti(OiPr)4/methanol or isopropanol systems. Application of dilution effects on the TiO2 catalysis leads to an increase in hydroxymethylation at the expense of the pinacol coupling.