Issue 25, 2019

Synthesis of fluorenyl alcohols via cooperative palladium/norbornene catalysis

Abstract

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.

Graphical abstract: Synthesis of fluorenyl alcohols via cooperative palladium/norbornene catalysis

Supplementary files

Article information

Article type
Paper
Submitted
10 Mot 2019
Accepted
06 Jan 2019
First published
06 Jan 2019

Org. Biomol. Chem., 2019,17, 6165-6173

Synthesis of fluorenyl alcohols via cooperative palladium/norbornene catalysis

A. Casnati, M. Fontana, E. Motti and N. Della Ca’, Org. Biomol. Chem., 2019, 17, 6165 DOI: 10.1039/C9OB01085H

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