Pentafluorobenzene → 4,4,5,5-Tetramethyl-2-(pentafluorophenyl)-1,3,2-dioxaborolane

HRID 1490558

Reaction equation

HRID 1490558 reaction equation
Fc1cc(F)c(F)c(F)c1F>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(F)c(F)c(F)c(F)c2F)OC1(C)C

Participants

6

Reactant 1

HCID 9696Pentafluorobenzene

Product 1

HCID 230657134,4,5,5-Tetramethyl-2-(pentafluorophenyl)-1,3,2-dioxaborolaneYield 87%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 122380799HCID 122380799, compoundReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 138539Cyclopentyl methyl etherSolvent

Conditions

Temperature
100 °C

Procedure

The general procedure A was followed using 1,2,3,4,5-pentafluorobenzene (55.4 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. 5n was obtained as colorless oil (128.2 mg, 87%) after purification by silica gel flash chromatography (EtOAc/PE=1:10 v/v).

Sources & evidence

ORD record
ord-54534f29ec2f4a67ac86529f28d9ea02
Source dataset
Borylation dataset from Roche

Linked notes

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