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(1-Chloroethyl)benzene → 4,4,5,5-tetramethyl-2-[4-[(E,3S)-3-phenylbut-1-enyl]phenyl]-1,3,2-dioxaborolane

HRID 1422366
Notes
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Reaction equation

HRID 1422366 reaction equation
CC(Cl)c1ccccc1.CC1(C)OB(c2ccc(/C=C/Br)cc2)OC1(C)C>CC(=O)N(C)C.COCCOC.[Cl][Ni][Cl].[I-].[Na+].c1ccc2c(c1)C[C@@H]1OC(C3(C4=N[C@@H]5c6ccccc6C[C@@H]5O4)CC3)=N[C@H]21>C[C@@H](/C=C/c1ccc(B2OC(C)(C)C(C)(C)O2)cc1)c1ccccc1
ParticipantsConditionsWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 12648(1-Chloroethyl)benzeneHCID 1350294392-[4-[(E)-2-bromoethenyl]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 1018996414,4,5,5-tetramethyl-2-[4-[(E,3S)-3-phenylbut-1-enyl]phenyl]-1,3,2-dioxaborolaneYield 62%

Reagents, catalysts & solvents 4

HCID 5238Sodium IodideReagentHCID 11245230(3aR,3a'R,8aS,8a'S)-2,2'-(Cyclopropane-1,1-diyl)bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole)CatalystHCID 15773433Dichloronickel;1,2-dimethoxyethaneCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Workup

  1. additionNo procedure recorded
  2. additionNo procedure recorded
  3. extractionKeep organic
  4. additionNo procedure recorded
  5. extractionKeep organic
  6. additionNo procedure recorded
  7. extractionKeep organic
  8. washNo procedure recorded
  9. dry with materialNo procedure recorded
  10. filtrationKeep filtrate
  11. concentrationNo procedure recorded

Sources & evidence

ORD record
ord-983567cbb5d244cab96293788fe8b9f7
Source dataset
Electroreductive Coupling of Alkenyl and Benzyl Halides
DOI
10.1021/acscatal.9b01785
Original link
View source

Reaction notes

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On this pageParticipantsConditionsWorkupSources & evidenceReaction notes