4-tert-Butylchlorobenzene → HCID 129946666, compound

HRID 1490568Notes

Reaction equation

HRID 1490568 reaction equation
CC(C)(C)c1ccc(Cl)cc1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC1CCCC1.C[OH2+].C[OH2+].[Ir].[Ir].c1ccc(N2B(B3Nc4ccccc4N3c3ccccn3)Nc3ccccc32)nc1>CC(C)(C)c1ccc(Cl)c(B2OC(C)(C)C(C)(C)O2)c1

Participants

6

Reactant 1

HCID 775944-tert-Butylchlorobenzene

Product 1

HCID 129946666HCID 129946666, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaboroleReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 138539Cyclopentyl methyl etherSolvent

Conditions

Temperature
100 °C

Procedure

The general procedure A was followed using 1-(tert-butyl)-4-chlorobenzene (79.1 ul, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 16 hours at 100 oC. 5aa was obtained as white solid (118.0 mg, 80%) after purification by silica gel flash chromatography (EtOAc/PE=1:50 v/v). m.p.: 73-75 oC.

Sources & evidence

ORD record
ord-db591dda52a34d67a62a70de910a941f
Source dataset
Borylation dataset from Roche

Reaction notes

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