16574-54-2

Upstream product

• 345-92-6 4,4'-Difluorobenzophenone 
• 80-70-6 N,N,N',N'-tetramethylguanidine 
• 39768-80-4 (4-Dimethylamino-phenyl)-(4-fluoro-phenyl)-methanol 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 1414852-71-3 MIDA ((4-fluorophenyl)oxomethyl)boronate 

Downstream Products

• 38695-24-8 4-(4-fluorobenzyl)-N,N-dimethylaniline 

Relevant academic research and scientific papers

Acylboronates in polarity-reversed generation of acyl palladium(II) intermediates

We report a catalytic cross-coupling process between aryl (pseudo)halides and boron-based acyl anion equivalents. This mode of acylboronate reactivity represents polarity reversal, which is supported by the observation of tetracoordinated boronate and acyl palladium(II) species by 11B, 31P NMR, and mass spectrometry. A broad scope of aliphatic and aromatic acylboronates has been examined, as well as a variety of aryl (pseudo)halides.

Iridium-Catalysed Reductive Deoxygenation of Ketones with Formic Acid as Traceless Hydride Donor

An iridium-catalysed deoxygenation of ketones and aldehydes is achieved, with formic acid as hydride donor and water as co-solvent. At low catalyst loading, a number of 4-(N,N-disubstituted amino) aryl ketones are readily deoxygenated in excellent yields and chemoselectivity. Numerous functional groups, especially phenolic and alcoholic hydroxyls, secondary amine, carboxylic acid, and alkyl chloride, are well tolerable. Geminally dideuterated alkanes are obtained with up to 90% D incorporation, when DCO2D and D2O are used in place of their hydrogenative counterparts. The activating 4-(N,N-disubstituted amino)aryl groups have been demonstrated to undergo a variety of useful transformations. The deoxygenative deuterations have been used to prepare a deuterated drug molecule Chlorambucil-4,4-d2. (Figure presented.).

Unusual aminations with tetramethylguanidine

Heating activated halobenzenes with 1,1,3,3-tetramethylguanidine affords mixtures of dimethylaminobenzenes and 2-aryl-1,1,3,3-tetramethylguanidines.