HCID 14511476, compound → HCID 178431010, compound

HRID 1490812Notes

Reaction equation

HRID 1490812 reaction equation
O=C(NC1CCc2ccccc21)C(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(c2ccc3c(c2)C(NC(=O)C(F)(F)F)CC3)OC1(C)C.CC1(C)OB(c2ccc3c(c2)CCC3NC(=O)C(F)(F)F)OC1(C)C

Participants

7

Reactant 1

HCID 14511476HCID 14511476, compound

Product 2

HCID 178431010HCID 178431010, compoundYield 33%HCID 178431015HCID 178431015, compoundYield 16%

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 N‐(2,3‐dihydro‐1H‐inden‐1‐yl)‐2,2,2‐trifluoroacetamide (57.3 mg, 0.25 mmol), B2pin2 (95 mg, 0.375 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and dtbpy (2.0 mg, 0.0075 mmol) in THF (1.25 mL). The reaction was stirred at 50 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 29:16:6:33 dimeta:meta1:meta2:para borylation in 84% yield.

Sources & evidence

ORD record
ord-f691df3f0f2040059acbb29c6f84a70b
Source dataset
Borylation dataset from Roche

Reaction notes

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