4-Chloroanisole → 4-Methoxybiphenyl

HRID 608052Notes

Reaction equation

HRID 608052 reaction equation
COc1ccc(Cl)cc1.OB(O)c1ccccc1>C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.C1COCCO1.O.O=P([O-])([O-])[O-].[K+].[K+].[K+].[Ni].c1ccc(-c2nn(-c3ccccc3)c(-c3ccccc3)c2-n2nccc2P(C2CCCCC2)C2CCCCC2)cc1>COc1ccc(-c2ccccc2)cc1

Participants

8

Reactant 2

HCID 121674-ChloroanisoleHCID 66827Phenylboronic Acid

Product 1

HCID 119434-MethoxybiphenylYield 3%

Reagents, catalysts & solvents 5

HCID 962WaterReagentHCID 62657Potassium Phosphate, TribasicReagentHCID 6433264Bis(1,5-cyclooctadiene)nickelCatalystHCID 534309145-(Dicyclohexylphosphino)-1',3',5'-triphenyl-[1,4']-bi-1H-pyrazoleCatalystHCID 312751,4-DioxaneSolvent4×

Conditions

Temperature
60 °C

Procedure

pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

Workup

  1. additionDilute with acetonitrile
  2. aliquotNo procedure recorded
  3. customDiluent solution was made in 1 L batches with 950 mL acetonitrile, 25 mL water, 25 mL glacial acetic acid, and 53 mg 4,4’-di-tert-butylbiphenyl as an external standard (0.2 equiv standard per reaction). Aliquot taken from each well (47 ul) is added into 753 ul of diluent solution

Sources & evidence

ORD record
ord-a5fd717815df47c68950386f232b4058
Source dataset
Ni-catalyzed Suzuki Miyaura cross-coupling
Original link
View source

Reaction notes

Loading…