HCID 4271591, compound → HCID 178447271, compound

HRID 1490766Notes

Reaction equation

HRID 1490766 reaction equation
CC(C)(C)C(=O)NCc1ccccc1C(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]>CC(C)(C)C(=O)NCc1cc(B2OC(C)(C)C(C)(C)O2)ccc1C(F)(F)F.CC(C)(C)C(=O)NCc1ccc(B2OC(C)(C)C(C)(C)O2)cc1C(F)(F)F

Participants

7

Reactant 1

HCID 4271591HCID 4271591, compound

Product 2

HCID 178447270HCID 178447270, compoundYield 43%HCID 178447271HCID 178447271, compoundYield 57%

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‐(trifluoromethyl)benzyl)pivalamide (64.8 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 1:1.3 meta:para borylation in 100% yield. As the para isomer could be characterised from the reaction with 1a the product was not isolated.

Sources & evidence

ORD record
ord-25414511bcb043d392730b6a6469467f
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…