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Direct access to benzo[b]fluorenes via a gold-catalysed A3-coupling strategy

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Abstract

A one-pot atom- and step-economical method for the synthesis of benzo[b]fluorenes, from aldehydes, alkynes and amines, proceeding via an A3-coupling/formal [4 + 2] thermal cyclization is described. The transformation generates water as the only by-product and three new carbon–carbon bonds are simultaneously formed. The scope was demonstrated by the synthesis of 32 benzo[b]fluorenes and, by specific designing of starting materials, regiocontrol could be accessed for some substrates.

Graphical abstract: Direct access to benzo[b]fluorenes via a gold-catalysed A3-coupling strategy

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Publication details

The article was received on 18 Feb 2019, accepted on 26 Mar 2019 and first published on 28 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00260J
Citation: Org. Chem. Front., 2019, Advance Article

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    Direct access to benzo[b]fluorenes via a gold-catalysed A3-coupling strategy

    D. M. Lustosa, P. Cieslik, D. Hartmann, T. Bruckhoff, M. Rudolph, F. Rominger and A. S. K. Hashmi, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00260J

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