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Merck
CN

940097

SPhos Pd G2 ChemBeads

solid

Synonym(s):

SPhos Pd G2, 2nd Generation SPhos Precatalyst ChemBeads, Chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) ChemBeads, SPhos-Pd-G2 ChemBeads, 2nd Generation SPhos Precatalyst, Chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II), SPhos-Pd-G2

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About This Item

Empirical Formula (Hill Notation):
C38H45ClNO2PPd
CAS Number:
1375325-64-6
Molecular Weight:
720.62
UNSPSC Code:
12352100
MDL number:
MFCD20264897
NACRES:
NA.21

Key Documents

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Product Name

SPhos Pd G2 ChemBeads,

InChI

1S/C26H35O2P.C12H10N.ClH.Pd/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;;/h9-11,16-21H,3-8,12-15H2,1-2H3;1-6,8-9H,13H2;1H;/q;;;+1/p-1

SMILES string

COC1=CC=CC(OC)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2.NC5=C(C6=C([Pd]Cl)C=CC=C6)C=CC=C5

InChI key

NOMWEFBAPVZIIP-UHFFFAOYSA-M

Quality Level

100

product line

ChemBeads

form

solid

composition

loading, 4-6 wt. %

mp

218 °C (dec.)

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Related Categories

Application

Application in Suzuki-Miyaura coupling:


Self-arylation of 1-alkyl-3-bromo-2-phenyl-2,1-borazaronaphthalenes to form 2,1-borazaronaphthols.


Suzuki–Miyaura coupling of β-borylated porphyrins with 2-iodoaniline.


Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles.


The cyanomethylation of (hetero)aryl halides or triflates as a tandem reaction for the synthesis of DNA-encoded libraries.[4] (37677078)

ChemBeads are chemical coated glass beads. ChemBeads offer improved flowability and chemical uniformity perfect for automated solid dispensing and high-throughput experimentation. The method of creating ChemBeads uses no other chemicals or surfactants allowing the user to accurately dispense sub-milligram amounts of chemical.

For general uses, product is also available in powdered form 753009

General description

The ChemBeads product of SPhos Pd G2, a second generation (G2) precatalyst in which phenethylamine based backbone of the (G1) complex is substituted with a biphenyl-based ligand. This improvement on the previous generation allows creating the active palladium species at room temperature with weak phosphate or carbonate bases. The catalyst proves remarkably adept at achieving a variety of Suzuki-Miyaura couplings among other cross-coupling reactions.s. Loaded on glass beads for use in high-throughput expermentation (HTE).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW5603

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Bryan T Ingoglia et al.
Tetrahedron, 75(32), 4199-4211 (2020-01-04)
Over the past three decades, Pd-catalyzed cross-coupling reactions have become a mainstay of organic synthesis. In particular, catalysts derived from biaryl monophosphines have shown wide utility in forming C-N bonds under mild reaction conditions. This work summarizes a variety of
Noah P Tu et al.
Angewandte Chemie (International ed. in English), 58(24), 7987-7991 (2019-03-21)
Technologies that enable rapid screening of diverse reaction conditions are of critical importance to methodology development and reaction optimization, especially when molecules of high complexity and scarcity are involved. The lack of a general solid dispensing method for chemical reagents
Ana L Aguirre et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 27(51), 12981-12986 (2021-07-08)
High-throughput experimentation (HTE) methods are central to modern medicinal chemistry. While many HTE approaches to C-N and Csp2 -Csp2 bonds are available, options for Csp2 -Csp3 bonds are limited. We report here how the adaptation of nickel-catalyzed cross-electrophile coupling of

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