901466
Mes-Umemoto reagent
≥95%
Synonyme(s) :
Dimesityl(trifluoromethyl)sulfonium trifluoromethanesulfonate, MacMillan trifluoromethylation reagent, dMesSCF3 reagent
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A propos de cet article
Formule empirique (notation de Hill) :
C20H22F6O3S2
Numéro CAS:
Poids moléculaire :
488.51
MDL number:
UNSPSC Code:
12161600
NACRES:
NA.22
Service technique
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Laissez-nous vous aiderQuality Level
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
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)
Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)
Classe de stockage
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
Numéro d'article de commerce international
| Référence | GTIN |
|---|---|
| 901466-1G | 04061835508242 |
| 901466-250MG | 04061835503506 |