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.

Synthesis of fluorenyl alcohols: Via cooperative palladium/norbornene catalysis / Casnati, A.; Fontana, M.; Motti, E.; Della Ca, N.. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 17:25(2019), pp. 6165-6173. [10.1039/c9ob01085h]

Synthesis of fluorenyl alcohols: Via cooperative palladium/norbornene catalysis

Motti E.
Supervision
;
Della Ca N.
Supervision
2019

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.
Synthesis of fluorenyl alcohols: Via cooperative palladium/norbornene catalysis / Casnati, A.; Fontana, M.; Motti, E.; Della Ca, N.. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 17:25(2019), pp. 6165-6173. [10.1039/c9ob01085h]
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11381/2862327
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