24314-35-0Relevant articles and documents
The Suzuki cross-coupling reaction for the synthesis of porphyrazine possessing bulky 2,5-(biphenyl-4-yl)pyrrol-1-yl substituents in the periphery
Szczolko, Wojciech,Wzgarda, Anna,Koczorowski, Tomasz,Wicher, Barbara,Sobotta, Lukasz,Gdaniec, Zofia,Gdaniec, Maria,Mielcarek, Jadwiga,Tykarska, Ewa,Goslinski, Tomasz
, p. 462 - 468 (2015)
The macrocyclization reactions led to higher-symmetry and lower-symmetry porphyrazines bearing peripheral 2,5-di(4′-chlorophenyl)pyrrol-1-yl and dimethylamino substituents, which were characterized using NMR and X-ray crystallography. The reactions were performed in the conditions of Linstead macrocyclization with magnesium n-butanolate in n-butanol with an addition of a malonitrile derivative in solid form or after dissolving it in DMF. It is interesting to note that the addition of DMF increases the total yield of the reaction from low to moderate, and forces the synthesis of the higher-symmetry over the lower-symmetry porphyrazine. The non-alternate order of peripheral substituents in lower-symmetry porphyrazine resulted in the non-equivalence of dimethylamino groups in 1H and 13C NMR spectra. The X-ray crystal structures of both porphyrazines revealed an almost perpendicular orientation of the bulky, 2,5-di(4′-chlorophenyl)pyrrol-1-yl substituents to the cores. Higher-symmetry porphyrazine was used in the Suzuki-Miyaura reaction with phenylboronic acid. This led with a high yield to the derivative possessing peripheral 2,5-di(biphenyl-4-yl)pyrrol-1-yl and dimethylamino substituents.
Copper(I)/DDQ-Mediated Double-Dehydrogenative Diels-Alder Reaction of Aryl Butenes with 1,4-Diketones and Indolones
Chen, Jie,Hu, Wei,Wang, Min,Xu, Wen-Lei,Zhao, Wei-Ming,Zhou, Ling
supporting information, p. 7169 - 7174 (2020/10/12)
A copper(I)/DDQ-mediated double-dehydrogenative Diels-Alder (DDDA) reaction of simple butenes with 1,4-diketones and indolones has been established for the first time. This strategy is based on a tandem double-dehydrogenation/Diels-Alder reaction from nonprefunctionalized starting materials, in which both a diene and dienophile were in situ generated via activation of fourfold inert C(sp3)-H bonds in one catalytic system.
Cyclotrimerization for the Synthesis of Cyclopropanes
Manna, Srimanta,Antonchick, Andrey P.
supporting information, p. 5290 - 5293 (2016/04/26)
The synthesis of small rings by functionalization of C(sp3)-H bonds remains a great challenge. We report for the first time a copper-catalyzed [1+1+1] cyclotrimerization of acetophenone derivatives under mild reaction conditions. The reaction has a broad scope for the stereoselective synthesis of cyclopropanes by trimerization of acetophenone. The developed transformation is based on an extraordinary copper-catalyzed cascade process that allows saturated carbocycles to be obtained for the first time by cyclotrimerization through functionalization of C(sp3)-H bonds. The cascade of sixfold C(sp3)-H bond functionalization allows the synthesis of cyclopropanes in a highly stereoselective approach. Give it a tri: Copper-catalyzed oxidative [1+1+1] cyclotrimerization of acetophenone derivatives under mild reaction conditions and with a broad reaction scope has been developed. This transformation is a radical cascade process that allows saturated carbocycles to be obtained by cyclotrimerization through functionalization of C(sp3)-H bonds.
