Chromium–Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols

Herein we describe an aerobic intramolecular dearomative coupling reaction of phenols using a catalytic system with the combination of a chromium–salen (Cr–salen) complex and a nitroxyl radical. This novel catalytic system enables the construction of a spirocyclic dienone product, which is a potentially useful intermediate for the synthesis of various natural products such as alkaloids and phenylpropanoids from bisphenol in good yield under mild reaction conditions (under O2 and ambient temperature). A preliminary mechanistic study suggests that this reaction system is promoted by a cooperative electron transfer between the Cr(III)–salen complex, nitroxyl radical and bisphenol substrate.

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ChemInform Abstract: Podand-Based Dimeric Chromium(III)-Salen Complex for Asymmetric Henry Reaction: Cooperative Catalysis Promoted by Complexation of Alkali Metal Ions.

ChemInform ◽

10.1002/chin.201520031 ◽

2015 ◽

Vol 46 (20) ◽

pp. no-no

Author(s):

Guang-Hui Ouyang ◽

Yan-Mei He ◽

Qing-Hua Fan

Keyword(s):

Alkali Metal ◽

Metal Ions ◽

Alkali Metal Ions ◽

Henry Reaction ◽

Cooperative Catalysis ◽

Salen Complex

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Chromium–Salen Complex / Nitroxyl Radical Cooperative Catalysis:A New Combination for Aerobic Intramolecular Dearomative Coupling of Phenols

10.26434/chemrxiv.12924005.v1 ◽

2020 ◽

Author(s):

Shota Nagasawa ◽

Shogo Fujiki ◽

Yusuke Sasano ◽

Yoshiharu Iwabuchi

Keyword(s):

Electron Transfer ◽

Catalytic System ◽

Good Yield ◽

Nitroxyl Radical ◽

Reaction System ◽

Coupling Reaction ◽

New Combination ◽

Mechanistic Study ◽

Reaction Conditions ◽

Salen Complex

Herein we describe an aerobic intramolecular dearomative coupling reaction of phenols using a catalytic system with the combination of a chromium–salen (Cr–salen) complex and a nitroxyl radical. This novel catalytic system enables the construction of a spirocyclic dienone product, which is a potentially useful intermediate for the synthesis of various natural products such as alkaloids and phenylpropanoids from bisphenol in good yield under mild reaction conditions (under O2 and ambient temperature). A preliminary mechanistic study suggests that this reaction system is promoted by a cooperative electron transfer between the Cr(III)–salen complex, nitroxyl radical and bisphenol substrate.

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Synthesis, Immobilization and Characterization of Chiral Metal-Salen Complex on Chloromethylated Crosslinked Polystyrene Microspheres

ACTA AGRONOMICA SINICA ◽

10.3724/sp.j.1095.2013.20185 ◽

2013 ◽

Vol 30 (3) ◽

pp. 276

Author(s):

Hao DING ◽

Baojiao GAO ◽

Wei CHENG

Keyword(s):

Polystyrene Microspheres ◽

Salen Complex ◽

Crosslinked Polystyrene ◽

Metal Salen Complex

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Chiral Mn(III) Salen Complex Immobilized on CuFe2O4@SiO2-NH2 NPs: A Cheap and Efficient Catalyst for N-arylation of Aryl Halides and Phenylboronic Acid Under Mild Conditions

Letters in Organic Chemistry ◽

10.2174/1570178616666190919110639 ◽

2020 ◽

Vol 17 (11) ◽

pp. 857-863

Author(s):

Mohammad Ali Nasseri ◽

Seyyedeh Ameneh Alavi ◽

Milad Kazemnejadi ◽

Ali Allahresani

Keyword(s):

Phenylboronic Acid ◽

Significant Loss ◽

Aryl Halides ◽

Coupling Reactions ◽

Efficient Catalyst ◽

Aryl Chlorides ◽

Mild Conditions ◽

Cross Coupling Reactions ◽

Salen Complex ◽

Ft Ir

A convenient and efficient chiral CuFe2O4@SiO2-Mn(III) Ch.salen nanocatalyst has been developed for the C-N cross-coupling reactions of aryl halides/ phenylboronic acid with N-heterocyclic compounds in water and/or DMSO under mild conditions. The catalyst could be applied for the N-arylation of a variety of nitrogen-containing heterocycles with aryl chlorides, bromides, iodides and phenylboronic acid under mild conditions. Moderate to good yields were achieved for all substrates. The structure of catalyst was characterized using various techniques including FT-IR, FE-SEM, EDX, XRD, TEM and TGA. The catalyst can be simply recovered and reused for several times without significant loss of activity.

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