Chemoselective Ruthenium-Catalyzed C–O Bond Activation: Orthogonality of Nickel- and Palladium-Catalyzed Reactions for the Synthesis of Polyaryl Fluorenones

Livia C. R. M. da Frota; Cédric Schneider; Mauro B. de Amorim; Alcides J. M. da Silva; Victor Snieckus

doi:10.1055/s-0036-1590985

Synlett, Inhaltsverzeichnis

Synlett 2017; 28(19): 2587-2593
DOI: 10.1055/s-0036-1590985

cluster

Chemoselective Ruthenium-Catalyzed C–O Bond Activation: Orthogonality of Nickel- and Palladium-Catalyzed Reactions for the Synthesis of Polyaryl Fluorenones

Livia C. R. M. da Frota

^aLaboratório de Catálise Orgânica, Instituto de Pesquisa de Produtos Naturais, Centro de Ciências da Saúde, Bl H, Ilha da Cidade Universitária, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ 21941-590, Brazil

^bDepartment of Chemistry, Queen’s University, Kingston, ON, K7L 3N6, Canada eMail: snieckus@chem-queensu.ca

,

Cédric Schneider

^cNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France

,

Mauro B. de Amorim

^dLaboratório de Modelagem Molecular e Espectroscopia Computacional, Instituto de Pesquisa de Produtos Naturais, Centro de Ciências da Saúde, Bl H, Ilha da Cidade Universitária, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ 21941-590, Brazil

,

Alcides J. M. da Silva

^aLaboratório de Catálise Orgânica, Instituto de Pesquisa de Produtos Naturais, Centro de Ciências da Saúde, Bl H, Ilha da Cidade Universitária, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ 21941-590, Brazil

,

Victor Snieckus*

^bDepartment of Chemistry, Queen’s University, Kingston, ON, K7L 3N6, Canada eMail: snieckus@chem-queensu.ca

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Published as part of the Cluster C–O Activation

Abstract

Ruthenium-catalyzed C–O bond activation/arylation of methoxy and O-carbamoyl-substituted fluorenones is reported. Established are new reactions of compound 1 (X = H) to aryl (2) and 1,8-diaryl (3) fluorenones. Orthogonal ruthenium-, palladium- and nickel-catalyzed reactions with Suzuki–Miyaura reactions to afford 1,4-diaryl (4) and 1,4,8-triaryl fluorenones (5) are also described. The ready availability of starting methoxy fluorenones by directed ortho and remote metalation tactics confers facility to the presented reactions which may find application in material science areas. DFT calculations have been performed to rationalize the lack of C–H bond reactivity in the ruthenium-catalyzed reaction.

Key words

C–O activation - fluorenone - ruthenium catalysis - nickel catalysis - palladium catalysis - polyarylation - orthogonal cross-coupling

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Referenzen

References and Notes

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Compound 1d has been previously prepared by a ten-step route:

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29 General Procedures to the Ru-Catalyzed Arylation of FluorenonesA dried Biotage microwave vial equipped with a magnetic stirring bar and a nitrogen inlet was sequentially charged with fluorenone (1, 0.5 mmol), boronic ester (6, 0.5–1 mmol), pinacolone (0.5 mL), and RuH₂(CO)(PPh₃)₃ (10 mol%). The reaction mixture was heated under MW irradiation at 150 °C for 2.5–8 h. The reaction mixture was extracted with EtOAc (15 mL), washed with brine, subjected to filtration, dried (Na₂SO₄), and concentrated under reduced pressure. Purification using flash column chromatography on silica gel (eluting with 1:9 hexanes/EtOAc) afforded product 2.1-(4-Fluorophenyl)-9H-fluoren-9-one (2g)Yellow solid, 91% yield; mp 156–158 °C (hexanes). ¹H NMR (400 MHz, CDCl₃): δ = 7.59 (d, J = 7.4 Hz, 1 H), 7.55 (d, J = 7.4 Hz, 1 H), 7.53–7.46 (m, 5 H), 7.29 (t, J = 7.2 Hz, 1 H), 7.16 (dd, J = 8.7, 1.2 Hz, 1 H), 7.12 (d, J = 8.7 Hz, 2 H). ¹³C NMR (101 MHz, CDCl₃): δ = 193.1 (C), 162.9 (d, ¹J_C–F = 247.3 Hz, C), 145.6 (C), 143.5 (C), 141.2 (C), 134.6 (CH), 134.3 (CH), 134.2 (C), 133.3 (d, ⁴J_C–F = 3.2 Hz, C), 131.5 (CH), 130.9 (d, ³J_C–F = 8.26 Hz, 2 CH), 129.6 (C), 129.3 (CH), 124.2 (CH), 120.1 (CH), 119.3 (CH), 114.87 (d, ²J_C–F = 21.5 Hz, 2 CH). IR (CH₂Cl₂): 1709, 1159 cm^–1. HRMS (ESI): m/z calcd for (C₁₉H₁₂FO)⁺: 275.0867; found: 275.0875.
30 During the preparation of this manuscript Yasui et al. reported a reductive cleavage of aryl O-carbamate under Rh-catalysis using isopropanol as a reductant, see: Yasui K. Higashino M. Chatani N. Tobisu M. Synlett 28 2017; in press;
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