4-Iodotoluene → HCID 3558444, compound

HRID 1394972Notes

Reaction equation

HRID 1394972 reaction equation
CC(C)(C)OC(=O)N1CCCC1C(=O)O.Cc1ccc(I)cc1>CC(C)(C)c1cc[n]2->[Ir+]34([c]5cc(F)cc(F)c5-c5ccc(C(F)(F)F)c[n]->35)([c]3cc(F)cc(F)c3-c3ccc(C(F)(F)F)c[n]->43)<-[n]3ccc(C(C)(C)C)cc3-c2c1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CN(C)C=O.COCCOC.F[P-](F)(F)(F)(F)F.O=C([O-])[O-].[Cl][Ni][Cl].[Cs+].[Cs+]>Cc1ccc(C2CCCN2C(=O)OC(C)(C)C)cc1

Participants

8

Reactant 2

HCID 122074-IodotolueneHCID 2684721-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 3558444HCID 3558444, compoundYield 78%

Reagents, catalysts & solvents 5

HCID 10796Cesium carbonateReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylCatalystHCID 15773433Dichloronickel;1,2-dimethoxyethaneCatalystHCID 178441129HCID 178441129, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

Prior to irradiation, the reaction mixture was degassed by bubbling argon for 20 minutes

Workup

  1. additiondiluted with saturated aqueous NaHCO3
  2. additionNo procedure recorded
  3. additionNo procedure recorded
  4. additionNo procedure recorded
  5. extractionextracted with Et2O (3 x 100 mL) · Keep organic
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. flash chromatographyFluka, 230-400 mesh, solvent system: 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-42e2098904ab491e9a348d65f0dddb47
Source dataset
Coupling of α-carboxyl sp3-carbons with aryl halides
Original link
View source

Reaction notes

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