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 1490547노트

반응식

HRID 1490547 반응식
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

참가 물질

6

반응물 1

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

생성물 1

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

시약·촉매·용매 4

HCID 2733548Bis(pinacolato)diborane시약HCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaborole시약HCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridium촉매HCID 138539Cyclopentyl methyl ether용매

반응 조건

온도
100 °C

실험 절차

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.

출처 및 근거

ORD 기록
ord-dcac225a30e24bb3ae1171b013e2207a
출처 데이터셋
Borylation dataset from Roche

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