Naphthoquinone-Directed C–H Annulation and Csp3–H Bond Cleavage: One-Pot Synthesis of Tetracyclic Naphthoxazoles
The Journal of Organic Chemistry2014Vol. 79(10), pp. 4553–4560
Citations Over TimeTop 16% of 2014 papers
Abstract
One-pot synthesis of tetracyclic naphthoxazole derivatives from electron-deficient naphthoquinones and alkynes was achieved via Rh(III)-catalyzed C-H activation and C(sp(3))-H bond cleavage for the first time. This approach proceeds through a tandem cascade process involving substrate tautomerization, C-H activation, oxidative addition, cyclization, and aromatization. In addition, broad substrate scope, simple starting materials, and steric tolerance make this strategy of great practicality.
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