Divergent oxidative dearomatization coupling reactions to construct polycyclic cyclohexadienones

Pu, Qian; Huo, Mingming; Liang, Guojuan; Bai, Lijuan; Chen, Genhui; Li, Hongjiao; Xiang, Peng; Zhou, Hui; Zhou, Jing

doi:10.1039/d2cc00183g

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2024

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Cited by 4 publications

References 33 publications

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Nitrooxylative Dearomatization Reaction of β‐Naphthols with Hypervalent Iodine Reagent

Zhang,

Li,

et al. 2024

Asian J Org Chem

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A catalyst‐free intermolecular dearomatization reaction of β‐naphthols with hypervalent‐iodine‐based nitrooxylating reagent is reported. Various nitrooxylated β‐naphthalenones bearing a quaternary carbon stereogenic center were obtained smoothly in good to excellent yields (up to 87 %) under mild conditions. This method features mild conditions, broad substrate scope and excellent chemoselectivity.

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Nitrooxylative Dearomatization Reaction of β‐Naphthols with Hypervalent Iodine Reagent

Zhang,

Li,

et al. 2024

Asian J Org Chem

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Halogen Bond Assisted Light Responsiveness of Para‐Quinone Methides for 1,6‐Conjugate Addition Reactions

Kumar,

Justin Thomas

2024

ChemCatChem

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The ability to change the essential characteristics of the molecular systems using light is highly promising and finds use in photocatalysis and materials chemistry. A critical requirement for such systems is that molecules should directly absorb light in the visible region. Though small molecule activation by visible light is challenging, they on complexation with certain species respond to visible light favourably. Herein, we disclose the catalytic application of CBr4 as a halogen bond donor catalyst to activate para‐quinone methides towards visible light photo‐catalysed reactions. This protocol facilitates 1,6‐conjugate addition reactions with various nucleophiles, forming C‐C and C‐O bonds in para‐quinone methides, yielding the desired products in good to excellent yields. Mechanistic investigations reveal that para‐quinone methide responds to visible light only when complexed with CBr4. The synthetic utility of this protocol is demonstrated through the one‐pot synthesis of spiro‐cyclohexadienone compounds from 2‐naphthol and para‐quinone methide.

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Six-membered ring systems: With O and/or S atoms

Santos,

Silva

2023

Progress in Heterocyclic Chemistry

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Divergent oxidative dearomatization coupling reactions to construct polycyclic cyclohexadienones

Abstract: Highly selective divergent oxidative dearomatization coupling reactions, in which the chemoselectivity is controlled by catalysts and bases, are reported herein. Three different kinds of polycyclic cyclohexadienones are produced from the...

Cited by 4 publications

References 33 publications

Nitrooxylative Dearomatization Reaction of β‐Naphthols with Hypervalent Iodine Reagent

Nitrooxylative Dearomatization Reaction of β‐Naphthols with Hypervalent Iodine Reagent

Halogen Bond Assisted Light Responsiveness of Para‐Quinone Methides for 1,6‐Conjugate Addition Reactions

Six-membered ring systems: With O and/or S atoms

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