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761435

Sigma-Aldrich

cataCXium® A Pd G3

greener alternative

95%

Synonyme(s) :

Mesylate[(di(1-adamantyl)-n-butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II), [(Di(1-adamantyl)-butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate, cataCXium-A-Pd-G3

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About This Item

Formule empirique (notation de Hill):
C37H52NO3PPdS
Numéro CAS:
Poids moléculaire :
728.27
Code UNSPSC :
12352300
ID de substance PubChem :
Nomenclature NACRES :
NA.22

Niveau de qualité

Pureté

95%

Forme

solid

Caractéristiques

generation 3

Capacité de réaction

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling

Pertinence de la réaction

reagent type: catalyst
reaction type: Cross Couplings

Score du produit alternatif plus écologique

old score: 16
new score: 2
Find out more about DOZN™ Scoring

Caractéristiques du produit alternatif plus écologique

Waste Prevention
Atom Economy
Safer Solvents and Auxiliaries
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

Impuretés

≤3% acetone

Pf

196-241 °C (decomposition)

Groupe fonctionnel

phosphine

Autre catégorie plus écologique

Chaîne SMILES 

CS(=O)(=O)O[Pd]c1ccccc1-c2ccccc2N.CCCCP([C@@]34C[C@@H]5C[C@@H](C[C@@H](C5)C3)C4)[C@@]67C[C@@H]8C[C@@H](C[C@@H](C8)C6)C7

InChI

1S/C24H39P.C12H10N.CH4O3S.Pd/c1-2-3-4-25(23-11-17-5-18(12-23)7-19(6-17)13-23)24-14-20-8-21(15-24)10-22(9-20)16-24;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h17-22H,2-16H2,1H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1/t17-,18+,19-,20-,21+,22-,23-,24-;;;

Clé InChI

REYVZCOGMIXVNX-DVBMAMJVSA-M

Description générale

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives. This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Safer Solvents and Auxiliaries” and “Atom Economy”. Click here to view its DOZN scorecard.

Application

cataCXium® A Pd G3 is a Buchwald third-generation precatalyst that can be used in:
  • Direct ortho-arylation of pyridinecarboxylic acids.
  • Catalyzing Suzuki–Miyaura cross-coupling in the synthesis of 1-heteroaryl-3-azabicyclo[3.1.0]hexanes.
  • Palladium-catalyzed carbonylative carboperfluoroalkylation of alkynes.
  • Suzuki–Miyaura coupling reaction of geminal bis(boryl)cyclopropanes in the synthesis of various gem-disubstituted cyclopropanes.
  • Boroperfluoroalkylation of terminal alkynes.
  • Copper-free Sonogashira coupling reaction of aromatic halides with alkynes to form C-C bond.
  • Suzuki cross-coupling between organotrifluoroborate and aryl halides.
For small scale and high throughput uses, product is also available as ChemBeads (928305)

Informations légales

cataCXium is a registered trademark of Umicore AG & Co. KG

Code de la classe de stockage

13 - Non Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Certificats d'analyse (COA)

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Direct ortho-Arylation of Pyridinecarboxylic Acids: Overcoming the Deactivating Effect of sp2-Nitrogen.
Johnston AJS, et al.
Organic Letters, 18(23), 6094-6097 (2016)
A Modular Approach to the Synthesis of gem-Disubstituted Cyclopropanes.
Harris MR, et al.
Organic Letters, 20(10), 2867-2871 (2018)
The use of carboxylic acids as traceless directing groups for regioselective C-H bond functionalisation.
Font M and Quibell
Chemical Communications (Cambridge, England), 53(41), 5584-5597 (2017)
Pd-Catalyzed Carbonylative Carboperfluoroalkylation of Alkynes. Through-Space 13C-19F Coupling as a Probe for Configuration Assignment of Fluoroalkyl-Substituted Olefins.
Domanski S, et al.
The Journal of Organic Chemistry, 82(15), 7998-8007 (2017)
Construction of 1-Heteroaryl-3-azabicyclo [3.1. 0] hexanes by sp3-sp2 Suzuki-Miyaura and Chan-Evans-Lam Coupling Reactions of Tertiary Trifluoroborates.
Harris MR, et al.
Organic Letters, 19(9), 2450-2453 (2017)

Articles

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form.

Multiple tools have been created to ensure your success with kit set up. Start with the more detailed guide to ensure you are comfortable with all of the steps before using the quick guides on the excel worksheet. Remember that while the technique is new, it is still organic chemistry and so the steps will seem easy once you try just one kit. It is just a new way of approaching something you are already very good at.

Materials Included in your KITALYSIS-24PD-2PK High-Throughput Screening Kit

G3 and G4 Buchwald palladium precatalysts are the newest air, moisture, and thermally stable crossing-coupling complexes used in bond formation for their versatility and high reactivity.

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