1,3,5-Trichlorobenzene → 4,4,5,5-Tetramethyl-2-(2,4,6-trichlorophenyl)-1,3,2-dioxaborolane

HRID 1490571Notes

Reaction equation

HRID 1490571 reaction equation
Clc1cc(Cl)cc(Cl)c1>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>CC1(C)OB(c2c(Cl)cc(Cl)cc2Cl)OC1(C)C

Participants

6

Reactant 1

HCID 79501,3,5-Trichlorobenzene

Product 1

HCID 219239064,4,5,5-Tetramethyl-2-(2,4,6-trichlorophenyl)-1,3,2-dioxaborolaneYield 49%

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
125 °C

Procedure

The general procedure A was followed using 1,3,5-trichlorobenzene (90.7 mg, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 24 hours at 125 oC. The 1H NMR conversion was 56%. 5ae was obtained as white solid (76.2 mg, 49%) after purification by silica gel flash chromatography (EtOAc/PE=1:100 v/v). m.p.: 129-131 oC.

Sources & evidence

ORD record
ord-7d6dac0c3e624fd1bd3caa82e3110eb0
Source dataset
Borylation dataset from Roche

Reaction notes

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