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901466

Sigma-Aldrich

Mes-Umemoto reagent

≥95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H22F6O3S2
CAS Number:
1895006-01-5
Molecular Weight:
488.51
MDL number:
MFCD31619197
UNSPSC Code:
12161600
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Photocatalysis

functional group

fluoro
thioether
triflate

storage temp.

−20°C

SMILES string

FC(F)(F)[S+](c2c(cc(cc2C)C)C)c1c(cc(cc1C)C)C.FC(F)(F)[S](=O)(=O)[O-]

InChI

1S/C19H22F3S.CHF3O3S/c1-11-7-13(3)17(14(4)8-11)23(19(20,21)22)18-15(5)9-12(2)10-16(18)6;2-1(3,4)8(5,6)7/h7-10H,1-6H3;(H,5,6,7)/q+1;/p-1

InChI key

HAYTWACXJNSBRL-UHFFFAOYSA-M

Related Categories

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ9903
SHBL0524
MKCF6515
70203024
40120001

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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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