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DOI: 10.1055/s-0037-1610134
Copper-Catalyzed Photoinduced Radical Domino Cyclization of Ynamides and Cyanamides: A Unified Entry to Rosettacin, Luotonin A, and Deoxyvasicinone
This work was supported by the Université libre de Bruxelles (ULB) and the Fédération Wallonie-Bruxelles (ARC Consolidator 2014-2019). H. B. and C. D. acknowledge the Fonds pour la formation à la Recherche dans l’Industrie et dans l’Agriculture (F.R.I.A.) for graduate fellowships.Publication History
Received: 09 March 2018
Accepted after revision: 09 April 2018
Publication Date:
28 May 2018 (online)
Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis
Abstract
A general and efficient procedure for the copper-catalyzed photoinduced radical domino cyclization of ynamides and cyanamides providing an efficient access to complex tri-, tetra- and pentacyclic nitrogen heterocycles is reported. Upon visible light irradiation in the presence of catalytic amounts of [(DPEphos)(bcp)Cu]PF6 and an amine, a range of unactivated aryl and alkyl iodides were shown to be smoothly transformed to the corresponding radical species, initiating the radical domino cyclization. This procedure provides a unified entry to rosettacin, luotonin A, and deoxyvasicinone that could be efficiently prepared in a limited number of steps.
Key words
copper catalysis - photocatalysis - radical cyclization - ynamides - cyanamides - rosettacin - luotonin A - deoxyvasicinoneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610134.
- Supporting Information
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