1,2-Dibromobenzene → 2-(3,4-Dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1490554Notes

Reaction equation

HRID 1490554 reaction equation
Brc1ccccc1Br>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(c2ccc(Br)c(Br)c2)OC1(C)C

Participants

6

Reactant 1

HCID 114141,2-Dibromobenzene

Product 1

HCID 467394342-(3,4-Dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 98%

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
80 °C

Procedure

The general procedure A was followed using 1,2-dibromobenzene (58.6 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 80 oC. 5j was obtained as colorless oil (178.2 mg, 98%) after purification by silica gel flash chromatography (EtOAc/PE=1:50 v/v).

Sources & evidence

ORD record
ord-baadeffb87484aadb662317cb7d23eb1
Source dataset
Borylation dataset from Roche

Reaction notes

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