p-Bromoacetophenone → tert-butyl N-[1-(4-acetylphenyl)-3-methylbutyl]-N-methylcarbamate

HRID 1394970Notes

Reaction equation

HRID 1394970 reaction equation
CC(=O)c1ccc(Br)cc1.CC(C)CC(C(=O)O)N(C)C(=O)OC(C)(C)C>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+]>CC(=O)c1ccc(C(CC(C)C)N(C)C(=O)OC(C)(C)C)cc1

Participants

8

Reactant 2

HCID 7466p-BromoacetophenoneHCID 333436N-(tert-butoxycarbonyl)-N-methylleucine

Product 1

HCID 126492167tert-butyl N-[1-(4-acetylphenyl)-3-methylbutyl]-N-methylcarbamateYield 91%

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: 9% ethyl acetate/hexane

Sources & evidence

ORD record
ord-660cb87b15dd4f7c815fc992b97bb989
Source dataset
Coupling of α-carboxyl sp3-carbons with aryl halides
Original link
View source

Reaction notes

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