Synthesis of fluorenyl alcohols via cooperative palladium/norbornene catalysis

Herein, we report a novel catalytic synthesis of substituted 9H-fluoren-9-ols starting from aryl iodides and secondary ortho-bromobenzyl alcohols in the presence of palladium/norbornene as a catalytic system. The present protocol exhibits high functional group tolerance, mild reaction conditions and...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-06, Vol.17 (25), p.6165-6173
Main Authors: Casnati, Alessandra, Fontana, Marco, Motti, Elena, Della Ca', Nicola
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Aromatic compounds
Catalysis
Chemical synthesis
Functional groups
Iodides
Oxidation
Palladium
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Summary:Herein, we report a novel catalytic synthesis of substituted 9H-fluoren-9-ols starting from aryl iodides and secondary ortho-bromobenzyl alcohols in the presence of palladium/norbornene as a catalytic system. The present protocol exhibits high functional group tolerance, mild reaction conditions and moderate to good yields. This transformation is based on two sequential pathways: (i) Pd(ii)-mediated oxidation of the secondary alcohol to the corresponding ketone and (ii) Pd(0)/norbornene-catalyzed reaction of the in situ generated ortho-bromoacetophenone with the aryl iodide.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01085h