Cobalt‐Catalyzed Oxidase C−H/N−H Alkyne Annulation: Mechanistic Insights and Access to Anticancer Agents |
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Authors: | Ruhuai Mei Hui Wang Svenja Warratz Prof Stuart A Macgregor Prof Dr Lutz Ackermann |
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Affiliation: | 1. Institut für Organische und Biomolekulare Chemie, Georg-August-Universit?t G?ttingen, G?ttingen, Germany;2. Institute of Chemical Sciences, Heriot-Watt University, Edinburgh, UK;3. http://www.ackermann.chemie.uni‐goettingen.de/
0000-0001-7034-8772
Institut für Organische und Biomolekulare Chemie, Georg-August-Universit?t G?ttingen, G?ttingen, Germany |
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Abstract: | Cp*‐free cobalt‐catalyzed alkyne annulations by C?H/N?H functionalizations were accomplished with molecular O2 as the sole oxidant. The user‐friendly oxidase strategy proved viable with various internal and terminal alkynes through kinetically relevant C?H cobaltation, providing among others step‐economical access to the anticancer topoisomerase‐I inhibitor 21,22‐dimethoxyrosettacin. DFT calculations suggest that electronic effects control the regioselectivity of the alkyne insertion step. |
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Keywords: | annulation C− H activation cobalt density functional calculations isoquinolones oxidase |
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