4-Chloroanisole → 4-Methoxybiphenyl

Reaction equation

COc1ccc(Cl)cc1.OB(O)c1ccccc1>C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.C1COCCO1.CC(C)(C)P(C1CCCCC1)C(C)(C)C.O.O=P([O-])([O-])[O-].[K+].[K+].[K+].[Ni]>COc1ccc(-c2ccccc2)cc1

Participants

Conditions

Temperature: 60 °C

Procedure

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

Workup

additionDilute with acetonitrile
aliquotNo procedure recorded
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-846c819274b849c5a76189f2d3f825b5
Source dataset: Ni-catalyzed Suzuki Miyaura cross-coupling
DOI: 10.26434/chemrxiv.14388557.v1
Original link: View source

Reaction notes

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Participants

Reactant 2

HCID 121674-Chloroanisole

HCID 66827Phenylboronic Acid

Product 1

HCID 119434-MethoxybiphenylYield 2%

Reagents, catalysts & solvents 5

HCID 962WaterReagent

HCID 62657Potassium Phosphate, TribasicReagent

HCID 4643321Di-tert-butylcyclohexylphosphineCatalyst

HCID 6433264Bis(1,5-cyclooctadiene)nickelCatalyst

HCID 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

additionDilute with acetonitrile
aliquotNo procedure recorded
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-846c819274b849c5a76189f2d3f825b5
Source dataset: Ni-catalyzed Suzuki Miyaura cross-coupling
DOI: 10.26434/chemrxiv.14388557.v1
Original link: View source

Reaction notes

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