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

HRID 1491142Notes

Reaction equation

HRID 1491142 reaction equation
CSc1cccc(N(C)C)c1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].Cc1ccc(C)cc1.FC(F)(F)C1COB(c2ccccc2-c2ccc(-c3ccccn3)nc2)O1.[Ir].[Ir]>CSc1cc(N(C)C)ccc1B1OC(C)(C)C(C)(C)O1

Participants

6

Reactant 1

HCID 20403482N,N-Dimethyl-3-(methylsulfanyl)aniline

Product 1

HCID 132510266N,N-dimethyl-3-methylsulfanyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineYield 76%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1349566232-Pyridin-2-yl-5-[2-[4-(trifluoromethyl)-1,3,2-dioxaborolan-2-yl]phenyl]pyridineReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
55 °C

Procedure

Ligand 3f: A mixture of ortho- and meta-borylated products (111 mg, 76% yield, ortho/meta + para = >30); ortho-borylated product 4h was obtained by further purification by GPC (100 mg, 68% yield), yellow oil;

Sources & evidence

ORD record
ord-1cb889e2f933486bac022f3a0a595351
Source dataset
Borylation dataset from Roche

Reaction notes

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