Chemistry is traditionally divided into organic and inorganic chemistry. Application In Synthesis of (1R,2R)-Cyclohexane-1,2-diamine. The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent,Which mentioned a new discovery about 20439-47-8
The reactions of pentafluoropyridine and 2,4,6-trifluoropyridine with a series of primary and secondary amines were studied. Whereas the nucleophilic aromatic substitution of pentafluoropyridine occurs with high regioselectivity in all cases, providing the expected 4-aminopyridine derivatives in excellent yields, the regioselectivity of 2,4,6-trifluoropyridine is dependent on the steric hindrance of the attacking nucleophile. Small nucleophiles such as morpholine attack the 4-position of the pyridine ring with high preference, but more bulky diamines attack the 2- and 4-positions leading to the formation of three regioisomeric products. (R,R)-1,2-Diaminocyclohexane as moderately bulky diamine reacted with 2,4,6-trifluoropyridine to afford the desired bis(4-aminopyridinyl)cyclohexane derivative in 30% yield. For hydrodefluorination two methods were examined. A two-step procedure employing hydrazine and subsequently copper(II) sulfate removed just one fluorine substituent, but is not sufficiently high yielding for the reduction of more complex substrates. With the system titanocene difluoride as pre-catalyst and diphenylsilane as reducing agent we were able to selectively remove fluorine substituents at positions C-2 and C-4 of a variety of 4-aminopyridine derivatives. This protocol allows the synthesis of compounds such as the divalent chiral 4-(dimethylamino)pyridine (DMAP) analogue (R,R)-trans-N,N’-dimethyl-N,N’-bis(pyridin-4-yl)cyclohexane-1,2-diamine with fair overall yield.
Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions.Application In Synthesis of (1R,2R)-Cyclohexane-1,2-diamine, you can also check out more blogs about20439-47-8
Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI