901466

Sigma-Aldrich

Mes-Umemoto reagent

≥95%

Synonym(s):
Dimesityl(trifluoromethyl)sulfonium trifluoromethanesulfonate, MacMillan trifluoromethylation reagent, dMesSCF3 reagent
Empirical Formula (Hill Notation):
C20H22F6O3S2
CAS Number:
Molecular Weight:
488.51

Quality Level

assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Photocatalysis

storage temp.

−20°C

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).

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

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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