HCID 70845390, compound → HCID 178431053, compound

HRID 1490770Notes

Reaction equation

HRID 1490770 reaction equation
CS(=O)(=O)NCCc1ccccc1C(F)(F)F>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>CC1(C)OB(c2ccc(C(F)(F)F)c(CCNS(C)(=O)=O)c2)OC1(C)C.CC1(C)OB(c2ccc(CCNS(C)(=O)=O)c(C(F)(F)F)c2)OC1(C)C

Participants

7

Reactant 1

HCID 70845390HCID 70845390, compound

Product 2

HCID 178431050HCID 178431050, compoundYield 40%HCID 178431053HCID 178431053, compoundYield 52%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Following general procedure F using 4b (66.8 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and dtbpy (2.0 mg, 0.0075 mmol) in THF (1.25 mL). Stirred in vial at 50 °C for 20 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 1.3:1 meta:para borylation in 97% yield. The crude product was purified by silica gel chromatography (40% EtOAc in Petroleum Ether 40‐60 o C) gave the title compound (as a 1.2:1 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (90 mg, 0.23 mmol, 92%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

Sources & evidence

ORD record
ord-2a4e6085cef94ca89a056c2502436433
Source dataset
Borylation dataset from Roche

Reaction notes

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