Copper-Catalyzed Cascade Substitution/Cyclization of N‑Isocyanates: A Synthesis of 1‑Aminobenzimidazolones

Copper-Catalyzed Cascade Substitution/Cyclization of N‑Isocyanates: A Synthesis of 1‑Aminobenzimidazolones

A copper-catalyzed cascade reaction of in situ generated nitrogen-substituted isocyanates (N-isocyanates) and 2-iodoanilines has been developed. The cascade relies on the base-catalyzed substitution of masked N-isocyanates, followed by Cu­(I)-catalyzed coupling to afford a variety of 1-aminobenzimid...

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Veröffentlicht in:Organic letters 2016-07, Vol.18 (14), p.3482-3485
Hauptverfasser: An, Jing, Alper, Howard, Beauchemin, André M
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Alper, Howard
Beauchemin, André M
description A copper-catalyzed cascade reaction of in situ generated nitrogen-substituted isocyanates (N-isocyanates) and 2-iodoanilines has been developed. The cascade relies on the base-catalyzed substitution of masked N-isocyanates, followed by Cu­(I)-catalyzed coupling to afford a variety of 1-aminobenzimidazolones in moderate to excellent yields. This is the first example of a transition-metal-catalyzed cascade reaction involving N-isocyanate intermediates.
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title Copper-Catalyzed Cascade Substitution/Cyclization of N‑Isocyanates: A Synthesis of 1‑Aminobenzimidazolones
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