24314-35-0Relevant academic research and scientific papers
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.
Asymmetric hydrogenation of 1,4-diketones: facile synthesis of enantiopure 1,4-diarylbutane-1,4-diols
Huang, Fanping,Shao, Pan-Lin,Song, Jingyuan,Wang, Jiang,Zhang, Xumu
supporting information, p. 262 - 265 (2022/01/06)
Owing to the biological significance and great synthetic value of 1,4-diarylbutane-1,4-diols and their derivatives, increasingly considerable attention has been paid to developing effective synthetic methods for chiral 1,4-diarylbutane-1,4-diols. We herei
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.
Synthesis of 1,4-Diketones via Titanium-Mediated Reductive Homocoupling of α-Haloketones
Le, Nathan N.,Rodriguez, Aimee M.,Alleyn, James R.,Gesinski, Michael R.
, p. 2195 - 2198 (2018/09/29)
1,4-Diketones have been synthesized via a reductive homocoupling of α-haloketones. Addition of a Grignard reagent to titanium(IV) isopropoxide affords a low-valent titanium(III) intermediate that is believed to mediate a radical dimerization reaction. The
Cyclotrimerization for the Synthesis of Cyclopropanes
Manna, Srimanta,Antonchick, Andrey P.
, 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.
A novel coupling reaction of α-halo ketones promoted by SmI3/CuI
Liu, Yongjun,Zhao, Hengmin,Tian, Guang,Du, Feng,Qi, Yan,Wen, Yonghong
, p. 26317 - 26322 (2016/03/25)
With SmI3 as the Lewis acid and catalyzed by CuI in DMF, α-haloketones were transformed unexpectedly into α-hydroxy-1,4-diketones in good to moderate yields. The mechanism was probed and a plausible reaction pathway was proposed. DMF was assumed to play a dual role both as a hydroxyl source and as a solvent.
Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane
Barrionuevo, Cecilia A.,Schmidt, Luciana C.,Argüello, Juan E.
, p. 4550 - 4555 (2016/06/09)
Cyclic 1,4-dicarbonyl compounds can be easily obtained by mixing a solution of aryl methyl or alkyl methyl ketone enolate anions with 1,3-diiodo-2,2-dimethylpropane in DMSO. This represents the first example of dimerization of ketone enolate anions using a simple diiodoalkane as a reagent followed by subsequent double alkylation with bis-iodide yielding a cyclopentane adduct. This methodology allows the use of a simple potassium tert-butoxide as a base at room temperature for the formation of three C-C bonds resulting in a relatively complex five-membered ring diketone structure under transition-metal-free conditions.
Visible-light-induced Ci-S bond activation: Facile access to 1,4-diketones from β-ketosulfones
Xuan, Jun,Feng, Zhu-Jia,Chen, Jia-Rong,Lu, Liang-Qiu,Xiao, Wen-Jing
supporting information, p. 3045 - 3049 (2014/03/21)
A novel method for the synthesis of 1,4-diketones from β-ketosulfones was developed by means of a visible light-induced Ci￡S bond activation process. Symmetrical and unsymmetrical 1,4-diketones can be easily prepared in moderate to good yields. A new and efficient method for the synthesis of 1,4-diketones from β-ketosulfones was developed by means of a visible-light-induced Ci￡S bond activation process (see scheme). Symmetrical and unsymmetrical 1,4-diketones can be easily prepared in moderate to good yields.
Polymer-stabilized palladium nanoparticles for the chemoselective transfer hydrogenation of α,β-unsaturated carbonyls: Single-step bottom-Up approach
Mahato, Sanjit K.,Ul Islam, Rafique,Acharya, Chiranjit,Witcomb, Michael J.,Mallick, Kaushik
, p. 1419 - 1426 (2014/05/20)
Polypyrrole stabilised palladium nanoparticles show good catalytic efficiency for the chemoselective transfer hydrogenation of α,β- unsaturated carbonyl compounds. The catalyst is very specific and selectively hydrogenates the olefins or acetylenes only,
Woollins reagent: A chemoselective reducing agent for 1,4-enediones and 1,4-ynediones to saturated 1,4-diones
Mandal, Madhumita,Chatterjee, Sourav,Jaisankar, Parasuraman
supporting information, p. 2615 - 2618,4 (2012/12/12)
Woollins reagent was found to act as a highly chemoselective reagent for the reduction of a wide range of 1,4-enediones and 1,4-ynediones in methanol to afford the corresponding saturated 1,4-diketones in good yields under mild reaction conditions.
