4-Chloroanisole → Ethyl 4'-methoxy[1,1'-biphenyl]-4-carboxylate

Reaction equation

CCOC(=O)c1ccc(B(O)O)cc1.COc1ccc(Cl)cc1>C1=C\CC/C=C\CC/1.C1=C\CC/C=C\CC/1.C1COCCO1.COc1ccc(C)c(-c2c(C(C)C)cc(C(C)C)cc2C(C)C)c1P(C(C)(C)C)C(C)(C)C.O.O=P([O-])([O-])[O-].[K+].[K+].[K+].[Ni]>CCOC(=O)c1ccc(-c2ccc(OC)cc2)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-c7b577c124204303bc843e42d5a2ba66
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 27343504-Ethoxycarbonylphenylboronic acid

Product 1

HCID 2764348Ethyl 4'-methoxy[1,1'-biphenyl]-4-carboxylateYield 0%

Reagents, catalysts & solvents 5

HCID 962WaterReagent

HCID 62657Potassium Phosphate, TribasicReagent

HCID 6433264Bis(1,5-cyclooctadiene)nickelCatalyst

HCID 56641709(2',4'-Diisopropyl-3-methoxy-6-methyl-6'-propyl-2-biphenylyl)[bis(2-methyl-2-propanyl)]phosphineCatalyst

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-c7b577c124204303bc843e42d5a2ba66
Source dataset: Ni-catalyzed Suzuki Miyaura cross-coupling
DOI: 10.26434/chemrxiv.14388557.v1
Original link: View source

Reaction notes

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