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939544

Sigma-Aldrich

(S)-tBuPHOX-Pd-MAH

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Synonym(s):

(S)-tert-Butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydrooxazole-palldium-maleicanhydride, (S)-tBuPHOX-Pd-maleic-anhydride

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About This Item

Empirical Formula (Hill Notation):
C29H28NO4PPd
CAS Number:
2966887-28-3
Molecular Weight:
591.93
UNSPSC Code:
12352100

form

powder

Quality Level

100

reaction suitability

core: palladium
reaction type: Trost Asymmetric Allylic Alkylation
reaction type: Tsuji-Trost Reaction
reagent type: catalyst

color

faint beige to dark beige-brown

SMILES string

CC(C)(C)[C@@H]1[N]([Pd]23C4([H])=C3([H])C(OC4=O)=O)=C(C5=CC=CC=C5[P]2(C6=CC=CC=C6)C7=CC=CC=C7)OC1

InChI

InChI=1S/C25H26NOP.C4H2O3.Pd/c1-25(2,3)23-18-27-24(26-23)21-16-10-11-17-22(21)28(19-12-6-4-7-13-19)20-14-8-5-9-15-20;5-3-1-2-4(6)7-3;/h4-17,23H,18H2,1-3H3;1-2H;/q;;-1/p+1/t23-;;/m1../s1

InChI key

FGSJOEKZZULTLF-MQWQBNKOSA-O

General description

(S)-tBuPHOX-Pd-MAH is a chiral Pd(0) precatalyst first produced in the group of David C. Leitch for asymmetric allylic alkylation reactions. The complex bears a chiral Pfaltz-Helmchen-Williams (PHOX) ligand as well as an easily diplaced maleic anhydride (MAH) ligand.

Application

Suitable for use in asymmetric allylic alkylation reactions such as the Tsuji–Trost reaction/Trost asymmetric allylic alkylation reaction. https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/cross-coupling/trost-ligands https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/cross-coupling/phox

Features and Benefits

(S)-tBuPHOX-Pd-MAH is a rare example of a chiral, isolable Pd(0) precatalyst for allylic alkylation reactions. Using a chiral single-component precatalyst instead of forming the chiral catalytic speices in-situ avoids activity, reproducibility, and/or selectivity problems arising from incomplete formation of the desired chiral catalyst.

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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

939544-BULK:
939544-1G:
939544-VAR:
939544-250MG:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3431

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Jingjun Huang et al.
Nature communications, 14(1), 8058-8058 (2023-12-06)
Stereoselective carbon-carbon bond formation via palladium-catalyzed asymmetric allylic alkylation is a crucial strategy to access chiral natural products and active pharmaceutical ingredients. However, catalysts based on the privileged Trost and Pfaltz-Helmchen-Williams PHOX ligands often require high loadings, specific preactivation protocols

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