Synthesis of indoles from aroyloxycarbamates with alkynes via decarboxylation/cyclization

An efficient Pd-catalyzed decarboxylation/cyclization of aroyloxycarbamates to realize substituted indoles has been disclosed. Terminal alkynes as the coupling partners lead to site specific 2-substituted indoles through two pathways, while internal alkynes with aroyloxycarbamates can be transformed...

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Veröffentlicht in:Organic & biomolecular chemistry 2018, Vol.16 (14), p.2421-2426
Hauptverfasser: Ma, Nuannuan, Li, Peihe, Wang, Zheng, Dai, Qipu, Hu, Changwen
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Sprache:eng
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Zusammenfassung:An efficient Pd-catalyzed decarboxylation/cyclization of aroyloxycarbamates to realize substituted indoles has been disclosed. Terminal alkynes as the coupling partners lead to site specific 2-substituted indoles through two pathways, while internal alkynes with aroyloxycarbamates can be transformed to 2,3-disubstituted indoles directly. This protocol is further demonstrated by the efficient synthesis of indoles as well as the success of employing inexpensive aryl acids as starting materials to construct C-N bonds by releasing CO2.
ISSN:1477-0520
1477-0539
DOI:10.1039/C8OB00086G