Wezeman, Tim published the artcileSynthesis of Non-Symmetrical and Atropisomeric Dibenzo[1,3]diazepines: Pd/CPhos-Catalyzed Direct Arylation of Bis-Aryl Aminals, Related Products of quinuclidine, the publication is Australian Journal of Chemistry (2015), 68(12), 1859-1865, database is CAplus.
Pd/CPhos-catalysis provides direct arylation/cyclization of methylene-linked bis[anilines] to dibenzo[1,3]diazepines which are both non-(C2)-sym. and axially chiral. Synthesis of the direct arylation substrates commences with substitution of (N-acyl)anilines to methylene Me sulfide derivatives, followed by halogenation/de-thiomethylation to N-(chloromethyl)anilines. These are substituted with a second aniline derivative, allowing modular preparation of (ortho-halo)aryl-aminal-linked arenes. The C-H functionalizing direct arylation conditions were adapted from Fagnou and others: substrates and potassium carbonate were heated in dimethylacetamide in the presence of palladium acetate and an electron-rich and sterically hindered biarylphosphine ligand, here CPhos. These conditions delivered the C1-(a)sym. dibenzo[1,3]diazepine targets, which, due to torsion around the axis of the newly formed biaryl bond, are also intrinsically atropisomeric. The axially twisted scaffold is known to impart special properties to ligands/catalysts when the products are further converted into the corresponding seven-membered ring-containing N-heterocyclic carbenes. Under optimized conditions the synthesis of the target compounds was achieved using 2′-(dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl[1,1′-biphenyl]-2,6-diamine (i.e., CPhos) and palladium acetate as ligand and catalyst combination. Key intermediates included N,N’-(methylene)-N,N’-bis(phenyl)acetamide derivatives (i.e., the above-mentioned aminals).
Australian Journal of Chemistry published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C5H12O2, Related Products of quinuclidine.
Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider