113386-14-4

Upstream product

• 1192-62-7 1-(2-furyl)-1-ethanone 
• 108-86-1 bromobenzene 
• 75488-41-4 1-(2-furyl)-1-phenylethylene 
• 98-86-2 acetophenone 
• 100-42-5 styrene 
• 110-00-9 furan 
• 174090-36-9 4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane 
• 98-85-1 1-Phenylethanol 
• 1257661-28-1 C₁₈H₂₃BO₃ 
• 93-92-5 1-phenylethyl acetate 

Relevant academic research and scientific papers

Iron(iii)-based ionic liquid-catalyzed regioselective benzylation of arenes and heteroarenes

An easily prepared Fe(iii)-derived Lewis acid ionic liquid ([C 4mim][FeCl4]), being comprised of 1-butyl-3-methyl imidazolium cation and tetrachloroferrate anion, was found to be an efficient, recyclable catalyst for benzylation of various arenes/heteroarenes into the diarylmethanes derivatives under mild reaction conditions without utilization of additional organic solvent. Interestingly, the acidity of [C 4mim][FeCl4] could account for its catalytic activity in promoting the Lewis acid-catalyzed alkylation. Notably, this type of Fe(iii)-based ionic liquid (IL) shows excellent stability, and could be easily recovered, and reused for five times without significant loss of its catalytic activity.

Rhodium-Catalyzed Regiodivergent Synthesis of Alkylboronates via Deoxygenative Hydroboration of Aryl Ketones: Mechanism and Origin of Selectivities

Here, we report an efficient rhodium-catalyzed deoxygenative borylation of ketones to synthesize alkylboronates, in which the regioselectivity can be switched by the choice of the ligand. The linear alkylboronates were obtained exclusively in the presence of P(nBu)3, and PPh2Me favored the formation of branched alkylboronates. The protocol also allows access to 1,1,2-triboronates from the readily available ketones. Mechanistic studies suggest that this Rh-catalyzed deoxygenative borylation of ketones goes through an alkene intermediate, which undergoes regiodivergent hydroboration to afford linear and branched alkylboronates. The different steric effects of PPh2Me and P(nBu)3 were found to be responsible for product selectivity by density functional theory calculations. The alkene intermediate can alternatively undergo sequential dehydrogenative borylation and hydroboration to deliver the triboronates.

Protodeboronation of tertiary boronic esters: Asymmetric synthesis of tertiary alkyl stereogenic centers

While tertiary boranes undergo efficient protodeboronation with carboxylic acids, tertiary boronic esters do not. Instead, we have discovered that CsF with 1.1 equiv of H2O (on tertiary diarylalkyl boronic esters) or TBAF?3H2O (on tertiary aryldialkyl boronic esters) effect highly efficient protodeboronation of tertiary boronic esters with essentially complete retention of configuration. Furthermore, substituting D2O for H2O provides ready access to deuterium-labeled enantioenriched tertiary alkanes. The methodology has been applied to a short synthesis of the sesquiterpene, (S)-turmerone.

Transition-metal-catalyzed benzylation of arenes and heteroarenes

Friedel-Crafts-type benzylation of various aromatic and heteroaromatic compounds with benzylic acetates, alcohols, and carbonates was promoted under mild reaction conditions by a series of Rh, Ir, Pd, and Pt catalysts (see scheme; R1 = H, Me; R2 = H, Cl, MeO; R3 = H, Ac, CO2Me). The desired products were obtained in high yields and with high selectivities.

Electrochemical Reduction of 1,1-Diaryl-substituted Ethenes in Dimethylformamide

The cathodic behaviour of 1,1-diaryl-substituted ethenes (Ar)PhC=CH2 (where Ar=phenyl-, 2-naphthyl-, 2-pyridyl-, 2-thienyl-, 2-furyl-) at a Hg cathode in N,N-dimethylformamide (DMF) and 0.1 mol dm-3 tetraethylammonium tetrafluoroborate (TEAF), was investigated by cyclic voltammetry and controlled potential electrolysis experiments.In cyclic voltammetry, at a potential scan rate of 0.2 V s-1, all substrates showed an irreversible reduction peak p,c) between -2.27 and -2.54 V vs. saturated calomel electrode (SCE)>.Controlled potential coulometries indicated that the apparent charge number of the process involved ranges from 1 to 2.The reduction products were characterised as (Ar)PhCH-Me (1-aryl-1-phenylethanes) and (Ar)PhCH-2-CHPh(Ar) (1,4-diaryl-1,4-diphenylbutanes).The charge number of the process and the ratio between the two different reduction products depended strongly on the structure and concentration of the substrate.Exhaustive electrolyses performed in the presence of variable amounts of D2O or in DMF allowed us to suggest that two distinct pathways are involved in the reduction process, leading to the monomeric and dimeric product, respectively.Hypotheses on the nature of the two reduction mechanisms are discussed.