2,6-Dichloropyridine → 2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

HRID 1490564Notes

Reaction equation

HRID 1490564 reaction equation
Clc1cccc(Cl)n1>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(c2cc(Cl)nc(Cl)c2)OC1(C)C

Participants

6

Reactant 1

HCID 169892,6-Dichloropyridine

Product 1

HCID 445163862,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineYield 97%

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 2,6-dichloropyridine (74.0 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 16 hours at 100 oC. 5w was obtained as white solid (132.9 mg, 97 %) after purification by silica gel flash chromatography (EtOAc/PE=1:5 v/v). m.p.: 118-119 oC

Sources & evidence

ORD record
ord-62ce0a6c98c4466e9745ea03d4597a44
Source dataset
Borylation dataset from Roche

Reaction notes

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