An efficient synthesis of N-fused
polycyclic and 2,3-disubstituted
indoles by copper-catalyzed direct annulation/acyl migration reaction
of enaminones is reported. This strategy features cheap and low loading
of the catalyst/ligand, readily available starting materials, and
good functional group compatibilities. Notably, allyl-containing substrates
are also tolerated, which allows the downstream derivatization toward
indole alkaloids.
An efficient synthesis
of N-fused polycyclic indoles
by a palladium-catalyzed annulation/acyl migration cascade reaction
is described. The reaction is ligand-free, scalable, and provides
access to a diverse range of useful indole scaffolds from readily
available starting materials. Supporting mechanistic studies indicate
that the reaction likely proceeds via an intramolecular α-arylation
mechanism. The synthetic utility of this protocol is demonstrated
by a gram-scale reaction and syntheses toward indole alkaloids and
a HSP90 inhibitor.
A palladium-catalyzed synthesis of enantiopure [1,1′-binaphthalene]-2,2′-dicarbonitriles from BINOL-bistriflates and zinc cyanide is reported. This cross-coupling reaction employs a 0.1–5 mol% catalyst loading, and is scalable and stereospecific. The synthetic applications of this reaction are demonstrated by product derivatizations and the synthesis of [1,1′-binaphthalene]-2,2′-bisoxazolines (BOXAX).
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