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Issue 6, 2013
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Synthesis of nitrodienes, nitrostyrenes, and nitrobiaryls through palladium-catalyzed couplings of β-nitrovinyl and o-nitroaryl thioethers

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Abstract

A highly efficient, base-free, mild protocol for the palladium-catalyzed, copper-activated desulfitative couplings of vinyl and aryl β-nitrothioethers generates a wide variety of conjugated nitroorganics. Orthogonality to traditional Suzuki–Miyaura coupling is demonstrated, as well as synthetic utility, through reductive Cadogan cyclization, for the formation of indoles, carbazoles, and pyrroles.

Graphical abstract: Synthesis of nitrodienes, nitrostyrenes, and nitrobiaryls through palladium-catalyzed couplings of β-nitrovinyl and o-nitroaryl thioethers

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Article information


Submitted
20 Mar 2013
Accepted
09 Apr 2013
First published
09 Apr 2013

Chem. Sci., 2013,4, 2670-2674
Article type
Edge Article

Synthesis of nitrodienes, nitrostyrenes, and nitrobiaryls through palladium-catalyzed couplings of β-nitrovinyl and o-nitroaryl thioethers

G. S. Creech and O. Kwon, Chem. Sci., 2013, 4, 2670
DOI: 10.1039/C3SC50773D

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