Benzamide → 4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 1490935

반응식

HRID 1490935 반응식
NC(=O)c1ccccc1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)O.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].O=c1ccc2cccc(-c3ccc(-c4ccccn4)nc3)c2[nH]1.[Ir].[Ir].[K]>CC1(C)OB(c2ccc(C(N)=O)cc2)OC1(C)C.CC1(C)OB(c2cccc(C(N)=O)c2)OC1(C)C

참가 물질

8

반응물 1

HCID 2331Benzamide

생성물 2

HCID 27605873-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide수율 9%HCID 27605884-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide수율 14%

시약·촉매·용매 5

HCID 2733548Bis(pinacolato)diborane시약HCID 1646813858-([2,2'-bipyridin]-5-yl)quinolin-2(1H)-one시약HCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridium촉매HCID 86639980Potassium tert-butoxide촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

In an argon filled glove box, a 5.0 mL wheaton microreactor was charged with [Ir(cod)(OMe)]2 (1.98 mg, 1.5 mol%), L1 ligand (2.1 mg, 3.5 mol%), B2pin2 (50.8 mg, 1.0 equiv.), KOtBu (1.0 mg, 4.5 mol%), and dry THF (1.0 mL). The reaction mixture was stirred for 2 minutes at room temperature. To this mixture, benzamide (24.2 mg, 0.2 mmol) was added. The microreactor was capped with a teflon pressure cap and placed into pre-heated aluminum block at 80 oC. After 12 h, (judged by GC/MS), we found that the conversion was 23% and meta/para ratio was 1/1.5.

출처 및 근거

ORD 기록
ord-8a61495c860141f1a8046698b9543528
출처 데이터셋
Borylation dataset from Roche

연결된 노트

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