A click strategy for the immobilization of palladium nanoparticles onto silica: efficient and recyclable catalysts for carbon–carbon bond formation under mild reaction conditions

The synthesis of silica-grafted palladium catalyst through “click” reaction of azide-functionalized silica with methylpropargylimidazolium bromide, for Heck and Suzuki–Miyaura coupling reactions.

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Modern Organic Synthesis in the Laboratory

10.1093/oso/9780195187984.001.0001 ◽

2008 ◽

Cited By ~ 1

Author(s):

Jie Jack Li ◽

Chris Limberakis ◽

Derek A. Pflum

Keyword(s):

Organic Chemistry ◽

Graduate Students ◽

Organic Synthesis ◽

Functional Group ◽

Bond Formation ◽

Reaction Conditions ◽

Carbon Bond ◽

Oxidation Reduction ◽

Carbon Carbon Bond ◽

Daunting Task

Searching for reaction in organic synthesis has been made much easier in the current age of computer databases. However, the dilemma now is which procedure one selects among the ocean of choices. Especially for novices in the laboratory, it becomes a daunting task to decide what reaction conditions to experiment with first in order to have the best chance of success. This collection intends to serve as an "older and wiser lab-mate" one could have by compiling many of the most commonly used experimental procedures in organic synthesis. With chapters that cover such topics as functional group manipulations, oxidation, reduction, and carbon-carbon bond formation, Modern Organic Synthesis in the Laboratory will be useful for both graduate students and professors in organic chemistry and medicinal chemists in the pharmaceutical and agrochemical industries.

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Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.12.289 ◽

2016 ◽

Vol 12 ◽

pp. 2898-2905 ◽

Cited By ~ 2

Author(s):

Michal Medvecký ◽

Igor Linder ◽

Luise Schefzig ◽

Hans-Ulrich Reissig ◽

Reinhold Zimmer

Keyword(s):

Click Reaction ◽

Cross Coupling ◽

Coupling Reactions ◽

High Efficacy ◽

Carbon Bond ◽

Bond Forming ◽

Cross Coupling Reactions ◽

Carbon Carbon Bond ◽

Palladium Catalyzed ◽

Oxazine Derivatives

Iodination of carbohydrate-derived 3,6-dihydro-2H-1,2-oxazines of type 3 using iodine and pyridine in DMF furnished 5-iodo-substituted 1,2-oxazine derivatives 4 with high efficacy. The alkenyl iodide moiety of 1,2-oxazine derivatives syn-4 and anti-4 was subsequently exploited for the introduction of new functionalities at the C-5 position by applying palladium-catalyzed carbon–carbon bond-forming reactions such as Sonogashira, Heck, or Suzuki coupling reactions as well as a cyanation reaction. These cross-coupling reactions led to a series of 5-alkynyl-, 5-alkenyl-, 5-aryl- and 5-cyano-substituted 1,2-oxazine derivatives being of considerable interest for further synthetic elaborations. This was exemplarily demonstrated by the hydrogenation of syn-21 and anti-24 and by a click reaction of a 5-alkynyl-substituted precursor.

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Palladium chloride catalyzed photochemical Heck reaction

Canadian Journal of Chemistry ◽

10.1139/cjc-2012-0377 ◽

2013 ◽

Vol 91 (5) ◽

pp. 348-351 ◽

Cited By ~ 5

Author(s):

Suresh B. Waghmode ◽

Sudhir S. Arbuj ◽

Bina N. Wani ◽

C.S. Gopinath

Keyword(s):

Visible Light ◽

Heck Reaction ◽

Palladium Nanoparticles ◽

Bond Formation ◽

Aryl Halides ◽

Palladium Chloride ◽

Carbon Bond ◽

Excellent Yield ◽

Carbon Carbon Bond ◽

Uv Visible

PdCl2 catalyzed carbon–carbon bond formation (Heck reaction) between substituted aryl halides and olefins was carried out without a ligand, under irradiation with UV–visible light. The results demonstrated that UV–visible light accelerated the rate of the reaction, leading to an excellent yield of corresponding products. The recovered palladium nanoparticles could be thermally recycled several times. PdCl2 gave excellent conversion up to the fifth addition of substrate.

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