Reaction #1385093

ord-8552b97ac613467a8875e93ec796cfec

Reaction equation

FC(F)(F)c1ccc(I)cc1
4-Iodobenzotrifluoride
C1COCCN1
Morpholine
→
Cn1c(=O)c2c(ncn2C)n(C)c1=O
Cn1c(=O)c2c(ncn2C)n(
FC(F)(F)c1cccc(N2CCOCC2)c1
FC(F)(F)c1cccc(N2CCO
FC(F)(F)c1ccc(N2CCOCC2)cc1
FC(F)(F)c1ccc(N2CCOC
Yield 4.3%

Reactants

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

Reagents

[Cu][Br]
COPPER(I) BROMIDE
CAS: 7787-70-4
C[Si](C)(C)[O-].[Na+]
Sodium trimethylsilanolate
CAS: 18027-10-6
O=C(N[C@H]1CCCC[C@@H]1NC(=O)c1ccccc1P(c1ccccc1)c1ccccc1)c1ccccc1P(c1ccccc1)c1ccccc1
(S,S)-DACH-PHENYL TROST LIGAND, 95%
CAS: 169689-05-8

Solvents

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

Conditions

Temperature
80°CELSIUS

Workup

  1. 1
    OtherThe 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.

Source

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