HCID 62491089, compound → HCID 178431092, compound

HRID 1490789Notes

Reaction equation

HRID 1490789 reaction equation
O=C(NCCc1ccccn1)C(F)(F)F>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CCCC[N+](CCCC)(CCCC)CCCC.C[OH2+].C[OH2+].Cc1ccc(-c2ccc(CS(=O)(=O)[O-])cn2)nc1.[Ir].[Ir]>CC1(C)OB(c2ccc(CCNC(=O)C(F)(F)F)nc2)OC1(C)C.CC1(C)OB(c2ccnc(CCNC(=O)C(F)(F)F)c2)OC1(C)C

Participants

7

Reactant 1

HCID 62491089HCID 62491089, compound

Product 2

HCID 178431049HCID 178431049, compoundYield 13%HCID 178431092HCID 178431092, compoundYield 77%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 165587889Tetrabutylazanium {5'-methyl-[2,2'-bipyridin]-5-yl}methanesulfonateReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

Following general procedure F using 4m (54.5 mg, 0.25 mmol), B2pin2 (95.2 mg, 0.375 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1a (3.8 mg, 0.0075 mmol) in THF (1.25 mL). Stirred in vial at 35 °C for 6 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 6.1:1:0.3 meta:para:di(3,5) borylation (overall meta:para borylation 4.7:1)  in 94% yield. Purification by silica gel chromatography proved not to be possible, leading to product decomposition. As such, the compounds were characterised from the crude, which contained pinacol borane impurity, and NMR yield was quoted in manuscript.

Sources & evidence

ORD record
ord-b47e5563af714079860cde41a9dfb09c
Source dataset
Borylation dataset from Roche

Reaction notes

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