Rhodium-catalyzed [2+2+2] cycloaddition reactions were studied using yne-allene-cyano substrates. A 10 mol% catalyst of [RhCl(PPh3)3] with 5 mol% Et3N in chlorobenzene at 120属C was used. The reaction conditions were examined for synthesizing substituted pyridines from alkynes, allenes and nitriles.
6. 6
NZ
X
Y
C
[RhCl(PPh3)3] (10 mol%)
Et3N (5 mol%)
Clorobenz竪
MW, 120尊C
N
Y
Z
X
Haraburda, E.; Lled坦, A.; Roglans, A.; Pla-Quintana, A. Org.
Lett. 2015, 17, 2882-2885.
7. 7
Study the viability of a rhodium-catalyzed [2+2+2] cycloaddition reaction on
the yne-allene-cyano substrate.
#2: Hello, I am Mrius, and now I will speak about my last work. The cycloaddition [2+2+2+] catalysed by rohodium involving allenes as substrate.
#4: The formation of rings is one of the most relevant processes in organic synthesis. The transition metal-catalyzed [2+2+2] cycloaddition is an efficient and sustainable method to build ring systems. This reaction type allows for carbocyclic and heterocyclic six-membered rings to be obtained in a single reaction step
#5: The number of substrates that can participate in this reaction has increased with the development of the [2+2+2] cycloaddition.
#6: Allenes are also an attractive substrate in [2+2+2] cycloadditions reactions. This compounds are characterized to have two pi orbitals that are roughly orthogonal and can show axial chirality.
#7: The METSO group reports the intramolecular [2+2+2] cycloaddition reaction of an cyano-yne-allene substrate.
#8: Following the study of Roglans and co-workers. I study the viability of the [2+2+2] cycloaddition reaction of the yne allene cyano substrated.
#9: First, I was syntetized the yne-allene-cyano substrated using the conditions of the slide. But the allene synthesis was difficult, its isolation in pure form is difficult. Moreover, when the reaction was scaled-up it did not work.
#10: When the allene was syntetised, I studied the [2+2+2] cycloaddition of this product using a rhodium complex as a catalyst. Two finals products were possible
#11: In function of the doble bond of the allene that participated in the reaction.
#12: However, the results were not as expected. I only observed the decomposition of the substrates.
#13: Hello, I am Mrius, and now I will speak about my last work. The cycloaddition [2+2+2+] catalysed by rohodium involving allenes as substrate.