(β-Oxoiminato)(phosphanyl)palladium Complexes as Highly Active Catalysts in Suzuki–Miyaura Coupling Reactions

2008 ◽  
Vol 2008 (2) ◽  
pp. 356-360 ◽  
Author(s):  
Dong-Hwan Lee ◽  
Ji-Young Jung ◽  
Ik-Mo Lee ◽  
Myung-Jong Jin
Keyword(s):  
Palladium Complexes ◽  
Coupling Reactions ◽  
Highly Active

Palladium immobilized on functionalized hypercrosslinked polymers: a highly active and recyclable catalyst for Suzuki–Miyaura coupling reactions in water

2019 ◽  
Vol 43 (31) ◽  
pp. 12206-12210 ◽  
Author(s):  
Xi Liu ◽  
Wei Xu ◽  
Dexuan Xiang ◽  
Zaixing Zhang ◽  
Dizhao Chen ◽  
...  
Keyword(s):  
Heterogeneous Catalysts ◽  
Palladium Complexes ◽  
Recyclable Catalyst ◽  
Cross Linking ◽  
Coupling Reactions ◽  
Highly Active ◽  
Hypercrosslinked Polymers

Three palladium complexes were synthesized via an external cross-linking reaction and found to be effective heterogeneous catalysts for the Suzuki–Miyaura reaction.

scholarly journals SYNTHESIS OF INDIVIDUAL ISOMERS OF 2-(3-CHLOROPROP-2-EN-1-YL)CYCLOHEXANONE

2019 ◽  
Vol 62 (8) ◽  
pp. 66-70
Author(s):  
Rinat N. Shakhmaev ◽  
Alisa Sh. Sunagatullina ◽  
Vladimir V. Zorin
Keyword(s):  
Phase Transfer ◽  
Palladium Complexes ◽  
Coupling Constants ◽  
Insect Pheromones ◽  
Coupling Reactions ◽  
Polycyclic Compounds ◽  
Cross Coupling Reactions ◽  
Highly Active ◽  
E And Z Isomers ◽  
High Yields

Recently, vinyl chlorides has been increasingly used as electrophilic partners in various cross-coupling reactions. In contrast to inaccessible and expensive vinyl bromides and iodides, in many cases vinyl chlorides are highly active in the presence of not only traditional palladium complexes, but also economical and safe compounds of iron, cobalt and nickel. Earlier, we reported on the development of new approaches to the getting of stereochemically pure (E)- and (Z)-vinyl chlorides and their successful use at the synthesis of medicines and insect pheromones. Continuing this work, an effective method of the synthesis of (E)- and (Z)-isomers of 2-(3-chloroprop-2-en-1-yl)cyclohexanone - convenient precursors of 2-(alk-2-en-1-yl)cyclohexanones, known flavors and intermediates in the synthesis of polycyclic compounds was developed. In the reaction of ethyl 2-oxocyclohexanecarboxylate with the (E)- and (Z)-isomers of 1,3-dichloropropene under the phase-transfer catalysis conditions in the presence of K2CO3, the corresponding (E)- and (Z)-isomers of ethyl 1-(3-chloroprop-2-en-1-yl)-2-oxocyclohexanecarboxylate were obtained in high yields (80-86%), without allyl rearrangement. The complete retention of the configuration of the chlorovinyl group is observed. Standard methods of the decarboxylation of isomers of ethyl 1-(3-chloroprop-2-en-1-yl)-2-oxocyclohexanecarboxylate under acidic or basic conditions result in very average yields of the corresponding chlorovinyl ketones. The best results were obtained by their decarbalkoxylation in slightly modernized Krapcho conditions. Carrying out reaction in N-methylpyrrolidone at 140-150 °C in the presence of 3 eq. LiCl and 2 eq. of H2O leads to individual (E)- and (Z)-isomers of 2-(3-chloroprop-2-en-1-yl)cyclohexanone in 79-82% yields and a stereochemical purity of ~ 99%. The structure of the obtained compounds were confirmed by HRGC, NMR, and GC/MS data. The configuration of the vinyl group was proved by the coupling constants of the vinyl hydrogens, equal to 13.2-13.4 and 7.0-7.3 Hz for the (E)- and (Z)-products, respectively, as well as by the downfield shift of the allyl carbon atom of trans-isomers by ~4 ppm as compared to the cis-analogs.

Cytostatic 6-Arylpurine Nucleosides II. Synthesis of Sugar-Modified Derivatives: 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-, 9-(5-Deoxy-β-D-ribofuranosyl)- and 9-(2,3-Dihydroxypropyl)-6-phenylpurines

2000 ◽  
Vol 65 (11) ◽  
pp. 1683-1697 ◽  
Author(s):  
Michal Hocek ◽  
Antonín Holý ◽  
Ivan Votruba ◽  
Hana Dvořáková
Keyword(s):  
Cross Coupling ◽  
Cytostatic Activity ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Highly Active ◽  
Phenylboronic Acids

9-(2-Deoxy-β-D-erythro-pentofuranosyl)-6-(4-substituted phenyl)purines, 9-(5-deoxy-β-D-ribofuranosyl)-6-(4-substituted phenyl)purines and 9-(2,3-dihydroxypropyl)-6-(4-substituted phenyl)purines were prepared by the Suzuki-Miyaura cross-coupling reactions of the corresponding protected 9-substituted 6-chloropurines with substituted phenylboronic acids followed by MeONa mediated deprotection. In contrast to the highly active 6-phenylpurine ribonucleosides, the title compounds did not show any considerable cytostatic activity.

Highly Active Heterogeneous PdCl2 /MOF Catalyst for Suzuki-Miyaura Cross-Coupling Reactions of Aryl Chloride

2020 ◽  
Vol 646 (15) ◽  
pp. 1336-1341 ◽  
Author(s):  
Xue-Fang Gong ◽  
Ling-Yan Zhang ◽  
Hui-Xin Zhang ◽  
Yu-Meng Cui ◽  
Fen-Chun Jin ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Aryl Chloride ◽  
Cross Coupling Reactions ◽  
Highly Active
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