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901466

Sigma-Aldrich

Mes-Umemoto reagent

≥95%

Sinónimos:

Dimesityl(trifluoromethyl)sulfonium trifluoromethanesulfonate, MacMillan trifluoromethylation reagent, dMesSCF3 reagent

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About This Item

Fórmula empírica (notación de Hill):
C20H22F6O3S2
Número de CAS:
1895006-01-5
Peso molecular:
488.51
UNSPSC Code:
12161600
NACRES:
NA.22

Quality Level

100

assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Photocatalysis

storage temp.

−20°C

Categorías relacionadas

Application

Under a dual catalytic copper/photoredox manifold, the Mes-Umemoto reagent has been demonstrated by the MacMillan lab to be an excellent reagent for the trifluoromethylation of alkyl halides and aryl halides to yield alkyl-CF3 and aryl-CF3 in high yields. In both cases, these reactions exhibit wide substrate scope with good functional group tolerance. More specifically, a variety of 5-membered and 6-membered heteroaryl halides can be readily converted to the corresponding trifluoromethylheteroarenes under mild conditions. To be use in conjunction with supersilanol (902489) and Ir photocatalyst (902217 or 902225).

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Other Notes

A radical approach to the copper oxidative addition problem:Trifluoromethylation of bromoarenes

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Referencia del producto
Descripción
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Ir[dFFppy]2-(4,4′-dCF3bpy)PF6, ≥95%

902225

Ir[dFMeppy]2-(4,4′-dCF3bpy)PF6, ≥95%

902489

Tris(trimethylsilyl)silanol, ≥95%

902802

2-(2,4-Difluorophenyl)-5-fluoropyridine, ≥95%

902810

4,4′-Bis(trifluoromethyl)-2,⋅2′-bipyridine

902829

2-(2,4-Difluorophenyl)-5-methylpyridine, ≥95%

904694

Ir(p-CF3-ppy)3, ≥95%

905917

(Ir[Me(Me)ppy]2(dtbpy))PF6

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
SHBL0524
MKCF6515
70203024
40120001
40120002

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Shi-Meng Wang et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 22(19), 6542-6546 (2016-03-08)
A Pd-catalyzed Suzuki cross-coupling of arylboronic acids with Yagupolskii-Umemoto reagents was explored. In contrary to trifluoromethylations, the Pd-catalyzed reaction of R-B(OH)2 and [Ar2 SCF3 ](+) [OTf](-) provided the arylation products (R-Ar) in good to high yields. The reaction confirms that
Chip Le et al.
Science (New York, N.Y.), 360(6392), 1010-1014 (2018-06-02)
Transition metal-catalyzed arene functionalization has been widely used for molecular synthesis over the past century. In this arena, copper catalysis has long been considered a privileged platform due to the propensity of high-valent copper to undergo reductive elimination with a

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