1,3-Benzenediamine, N1,N1,N3,N3-tetramethyl- → N1,N1,N3,N3-Tetramethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzenediamine

HRID 1490547Notes

Reaction equation

HRID 1490547 reaction equation
CN(C)c1cccc(N(C)C)c1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC1CCCC1.C[OH2+].C[OH2+].[Ir].[Ir].c1ccc(N2B(B3Nc4ccccc4N3c3ccccn3)Nc3ccccc32)nc1>CN(C)c1cc(B2OC(C)(C)C(C)(C)O2)cc(N(C)C)c1

Participants

6

Reactant 1

HCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-

Product 1

HCID 20775197N1,N1,N3,N3-Tetramethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzenediamineYield 93%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaboroleReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 138539Cyclopentyl methyl etherSolvent

Conditions

Temperature
100 °C

Procedure

The general procedure A was followed using N1 ,N1 ,N3 ,N3 -tetramethylbenzene-1,3-diamine (84 uL, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 24 hours at 100 oC. 5b was obtained as white solid (135.2 mg, 93%) after purification by silica gel flash chromatography (EtOAc/PE=1:20 v/v). m.p.: 178-180 °C.

Sources & evidence

ORD record
ord-dcac225a30e24bb3ae1171b013e2207a
Source dataset
Borylation dataset from Roche

Reaction notes

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