N,N-Dimethylaniline → N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

HRID 1490490Notes

Reaction equation

HRID 1490490 reaction equation
CN(C)c1ccccc1>B1Oc2ccccc2O1.CC(C)(O)C(C)(C)O.CCN(CC)CC.Cc1ccccc1.Fc1c(F)c(F)c(B(c2c(F)c(F)c(F)c(F)c2F)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F>CN(C)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1

Participants

7

Reactant 1

HCID 949N,N-Dimethylaniline

Product 1

HCID 2758659N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineYield 83%

Reagents, catalysts & solvents 5

HCID 6425PinacolReagentHCID 8471TriethylamineReagentHCID 67506CatecholboraneReagentHCID 582056Tris(pentafluorophenyl)boraneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Prepared from N,N-dimethylaniline (1a, 24.2 mg, 0.200 mmol, 1.00 equiv) and catBH (36.0 mg, 0.300 mmol, 1.50 equiv) according to GP 1. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 3a (41.0 mg, 83%) as a white solid.

Sources & evidence

ORD record
ord-34b2e90e8bac42c8b325e7edc6645b46
Source dataset
Borylation dataset from Roche

Reaction notes

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