2-Chlorotoluene → 2-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1490929Notes

Reaction equation

HRID 1490929 reaction equation
Cc1ccccc1Cl>C1=CCCC=CCC1.C1=CCCC=CCC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC(C)(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>Cc1cc(B2OC(C)(C)C(C)(C)O2)ccc1Cl.Cc1ccc(B2OC(C)(C)C(C)(C)O2)cc1Cl

Participants

7

Reactant 1

HCID 72382-Chlorotoluene

Product 2

HCID 37676412-(4-Chloro-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 34%HCID 234451072-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 66%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
25 °C

Procedure

General procedure C was applied to 1-chloro-2-methylbenzene 15e(51 mg, 0.4mmol). The reaction mixture was stirred at room temperature for 16hgiving a conversion of >99% (GC-MS) and 16eand17ein a 34:66mixture (1H NMR spectrum).

Sources & evidence

ORD record
ord-d0ca44bdeb6f41f09925b6db044f6c30
Source dataset
Borylation dataset from Roche

Reaction notes

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