A Lewis acid-catalyzed intermolecular 1,6-hydroolefination of p-quinone methides with styrenes leading to vinyl diarylmethanes and indenes has been developed. This protocol was also elaborated to the total synthesis of (±)-isopaucifloral F. Besides, interestingly, the reaction between 2-alkynylated p-quinone methides and styrenes provided a straightforward access to dihydrobenzo[ a]fluorene derivatives in one pot with 100% atom-economy.
A simple and efficient protocol to access diarylmethyl thioethers through the triflic acid catalyzed vinylogous Michael addition of aromatic and aliphatic thiols to p‐quinone methides under continuous‐flow conditions by using a microreactor was developed.
An efficient and mild protocol for the direct construction of aryl- and alkyl-substituted isoquinolines has been realized through silver nitrate catalyzed aromatic annulation of o-(1-alkynyl)arylaldehydes and ketones with ammonium acetate. The salient feature of this methodology is that this annulation could be effected at room temperature leading to a wide range of isoquinoline derivatives in good to excellent yields. Additionally, this approach has been employed to the synthesis of biologically important isoquinoline alkaloids such as berberine and palmatine.
An effective method for the construction of the structurally complex fused cyclohepta[ b]indole core has been developed through an intermolecular 1,6-conjugate addition of indoles to 2-alkynyl p-quinone methides followed by an intramolecular electrophilic cyclization under oxophilic and alkynophilic gold catalysis.
A Cu-catalyzed one-pot approach has been developed for the synthesis of 1,2,3-triazole-fused tricyclic heterocycles. This tandem approach actually involves the 1,6-conjugate addition of MeSiN to o-alkynylated p-quinone methides followed by an intramolecular [3+2]-cycloaddition reaction. This protocol allowed us to access a wide range of 1,2,3-trazole-fused isoindoline derivatives in moderate to good yields.
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