761435

Sigma-Aldrich

cataCXium® A Pd G3

95%

Synonym(s):
cataCXium-A-Pd-G3, 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
Empirical Formula (Hill Notation):
C37H52NO3PPdS
CAS Number:
Molecular Weight:
728.27
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

95%

feature

generation 3

reaction suitability

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
reagent type: catalyst
reaction type: Cross Couplings

impurities

≤3% acetone

mp

196-241 °C (decomposition)

functional group

phosphine

SMILES string

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-;;;

InChI key

REYVZCOGMIXVNX-DVBMAMJVSA-M

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.

Packaging

250 mg in glass bottle
1, 5 g in glass bottle

Legal Information

cataCXium is a registered trademark of Evonik Degussa GmbH

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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)
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)
Direct ortho-Arylation of Pyridinecarboxylic Acids: Overcoming the Deactivating Effect of sp2-Nitrogen.
Johnston AJS, et al.
Organic Letters, 18(23), 6094-6097 (2016)
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)
Articles
All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form.
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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.
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Materials Included in your KITALYSIS-24PD-2PK High-Throughput Screening Kit
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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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