2-Cyclohexen-1-one → 2-Phenylcyclohexanone

HRID 1410311Notes

Reaction equation

[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[C:8]1(B(O)O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:8]1([CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][C:1]2=[O:7])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Reactant 2

HCID 135942-Cyclohexen-1-one

HCID 66827Phenylboronic Acid

Product 1

HCID 955922-Phenylcyclohexanone

Procedure

Lastly, to examine the utility of the catalyst on a somewhat larger scale, the reaction of cyclohexenone with phenylboronic acid was performed on a 20 mmol scale and the product 2-phenyl cyclohexanone was isolated in identical yield (83%) to the small-scale reaction (Table 1, entry 5). Thus, the ligands described herein may have practical application in larger scale reactions.

Sources & evidence

ORD record: ord-a251faf949654e0eaaea9d7594335054
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921486B2

Reaction notes

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