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804371

Sigma-Aldrich

Fro-DO, mixture of diastereomers

97%

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About This Item

Empirical Formula (Hill Notation):
C24H22N2O6S2
Molecular Weight:
498.57
UNSPSC Code:
12161600
PubChem Substance ID:
329768865
NACRES:
NA.22

Quality Level

100

Assay

97%

form

powder

reaction suitability

core: nickel
reagent type: catalyst

SMILES string

O=C(N([C@H](C(C=CC=C1)=C1C2)[C@H]2C3)S3(=O)=O)/C=C/C(N4[C@H](C(C=CC=C5)=C5C6)[C@H]6CS4(=O)=O)=O

InChI

1S/C24H22N2O6S2/c27-21(25-23-17(13-33(25,29)30)11-15-5-1-3-7-19(15)23)9-10-22(28)26-24-18(14-34(26,31)32)12-16-6-2-4-8-20(16)24/h1-10,17-18,23-24H,11-14H2/b10-9+/t17-,18-,23+,24+/m1/s1

InChI key

CZVFUQRTDAQUQL-SKLQJEMHSA-N

Application

Enables the generation of quaternary centers by Ni-catalyzed cross coupling with aziridines.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Chung-Yang Dennis Huang et al.
Journal of the American Chemical Society, 137(17), 5638-5641 (2015-04-17)
A Ni-catalyzed Negishi cross-coupling with 1,1-disubstituted styrenyl aziridines has been developed. This method delivers valuable β-substituted phenethylamines via a challenging reductive elimination that affords a quaternary carbon. A novel electron-deficient olefin ligand, Fro-DO, proved crucial for achieving high rates and

Related Content

Doyle Group – Professor Product Portal

Research in the Doyle group focuses on two areas: nucleophilic fluorination and nickel catalysis. The Doyle group has developed several reagents that advance these research areas. In fluorination, 2-pyridinesulfonyl fluoride (PyFluor) can be used for the mild deoxyfluorination of primary and secondary alcohols, a procedure which is normally accomplished by the sensitive reagent DAST. In nickel catalysis, the Doyle group has developed a modular, air-stable nickel precatalyst, [(TMEDA)Ni(o-tolyl)Cl], which has broad utility for a wide variety of reactions. This precatalyst can be used in place of Ni(cod)2, NiCl2, as well as other reported precatalysts. Doyle has also reported electron-deficient olefin ligands as a new class of ligand for accelerated reductive elimination. In particular, the sultam-derived ligand Fro-DO has been found to be critical for high yields in the cross-coupling of tertiary aziridines to form quaternary centers.

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