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 1490547ノート

反応式

HRID 1490547 の反応式
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

参加物

6

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 2733548Bis(pinacolato)diborane試薬HCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaborole試薬HCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridium触媒HCID 138539Cyclopentyl methyl ether溶媒

反応条件

温度
100 °C

実験手順

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.

出典と根拠

ORDレコード
ord-dcac225a30e24bb3ae1171b013e2207a
出典データセット
Borylation dataset from Roche

反応ノート

読み込み中…