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Sigma-Aldrich

cataCXium® A Pd G3

95%

Synonym(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

Empirical Formula (Hill Notation):
C37H52NO3PPdS
CAS Number:
1651823-59-4
Molecular Weight:
728.27
UNSPSC Code:
12352300
PubChem Substance ID:
329766937
NACRES:
NA.22

Quality Level

100

assay

95%

form

solid

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

Related Categories

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)

Legal Information

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

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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 boroperfluoroalkylation of alkynes opens a route to one-pot reductive carboperfluoroalkylation of alkynes with perfluoroalkyl and aryl iodides
Domannski S, et al.
Organic Letters, 13, 5021-5025 (2019)
Copper-free Sonogashira cross-coupling reactions: an overview
Mohajer F, et al.
Royal Society of Chemistry Advances, 11, 6885-6925 (2021)
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)
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