Reaktion #1385024

ord-41f3ff25ff06457dba590d14b48aeeb1

Reaktionsgleichung

FC(F)(F)c1ccc(I)cc1
4-Iodobenzotrifluoride
C1COCCN1
Morpholine
→
FC(F)(F)c1cccc(N2CCOCC2)c1
FC(F)(F)c1cccc(N2CCO
FC(F)(F)c1ccc(N2CCOCC2)cc1
FC(F)(F)c1ccc(N2CCOC
Ausbeute 5.2%
Cn1c(=O)c2c(ncn2C)n(C)c1=O
Cn1c(=O)c2c(ncn2C)n(

Edukte

FC(F)(F)c1ccc(I)cc1
4-Iodobenzotrifluoride
CAS: 455-13-0
C1COCCN1
Morpholine
CAS: 110-91-8

Reagenzien

CC1=CC(C)=[O]->[Cu]2([O]1)[O]C(C)=CC(C)=[O]->2
Cu(acac)2
CAS: 13395-16-9
CC(C)(C)[O-].[K+]
potassium tert-butoxide
CAS: 865-47-4
O=C(O)C(=O)Nc1c(F)c(F)c(F)c(F)c1F
2,3,4,5,6-Pentafluoroanilino(oxo)acetic acid
CAS: 1454681-04-9

Lösungsmittel

CS(C)=O
dmso
CS(C)=O
dmso
CS(C)=O
dmso
CS(C)=O
dmso
CS(C)=O
dmso

Reaktionsbedingungen

Temperatur
80°CELSIUS

Aufarbeitung

  1. 1
    SonstigeThe foil sealing tape was removed from the plate.
  2. 2
    workup.ADDITION3 μL of a 0.0667 M solution of caffeine in DMSO was added to each reaction well using an SPT Labtech Mosquito® liquid handling robot
  3. 3
    FiltrationThe plates were then centrifuged for 15 to 20 seconds.
  4. 4
    workup.ALIQUOTFollowing centrifugation, 500 nL of the resultant mixture from each well was carefully dispensed into four 384-well analytical plates (Analytical Sales # 38435) using an SPT Labtech Mosquito® liquid handling robot. Each well of these analytical plates contained 30 μL of DMSO with 0.1% acetic acid, pre-dosed by OpenTrons, to facilitate analysis.

Quelle

DOI: 10.1021/jacs.6c05959High-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions