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

Literature Information

Publication Date 2019-03-28
DOI 10.1039/C9QO00260J
Impact Factor 5.281
Authors

Danilo M. Lustosa, Patrick Cieslik, Deborah Hartmann, Tim Bruckhoff, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi


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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.

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Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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