Reaktion #1577955

ord-b22003b7c65748a7a5209d4fd3292b64

Reaktionsgleichung

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Edukte

O=C(NCCc1ccccc1I)C(F)(F)F

CAS: 934672-80-7

Reagenzien

C1=CCCC=CCC1.C1=CCCC=CCC1.C[OH

CAS: 12148-71-9

CCCC[N+](CCCC)(CCCC)CCCC.Cc1cc

CAS: 2007932-96-7

CC1(C)OB(B2OC(C)(C)C(C)(C)O2)O

CAS: 73183-34-3

Lösungsmittel

C1CCOC1

CAS: 109-99-9

Reaktionsbedingungen

Temperatur

50°CELSIUS

Vorschrift

Following general procedure F using 4d (86 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1a (3.8 mg, 0.0075 mmol) in THF (1.25 mL). Stirred in vial at 50 °C for 20 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 5.7:1 meta:para borylation in 85% yield (12% starting material remaining). The crude product was purified by silica gel chromatography (15% EtOAc in Petroleum Ether 40‐60 o C) gave the title compound (as a 5.4:1 mixture of meta:para ratio, as determined by 1 H NMR) as a yellowish oil (79 mg, 0.17 mmol, 68%).

Quelle

DOI: 10.1002/anie.201708967Borylation dataset from Roche