HCID 3869638, compound → HCID 178427431, compound

HRID 1490760Notes

Reaction equation

HRID 1490760 reaction equation
Cc1ccc(S(=O)(=O)NCc2ccccc2C(F)(F)F)cc1>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]>Cc1ccc(S(=O)(=O)NCc2cc(B3OC(C)(C)C(C)(C)O3)ccc2C(F)(F)F)cc1.Cc1ccc(S(=O)(=O)NCc2ccc(B3OC(C)(C)C(C)(C)O3)cc2C(F)(F)F)cc1

Participants

7

Reactant 1

HCID 3869638HCID 3869638, compound

Product 2

HCID 178427430HCID 178427430, compoundYield 28%HCID 178427431HCID 178427431, compoundYield 56%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
35 °C

Procedure

Following general procedure F using 4‐methyl‐N‐(2‐(trifluoromethyl)benzyl)benzenesulfonamide (82.3 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 35 °C* for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 1:2 meta:para borylation in 84% yield. As the para isomer could be characterised from the reaction with 1a the product was not isolated.

Sources & evidence

ORD record
ord-6981e13bd7c14dcc934ee4bdf61b853f
Source dataset
Borylation dataset from Roche

Reaction notes

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