4.7 Article

Tandem Synthesis of 1,3-Disubstituted Naphthalenes via TfOH-Promoted Directed-Aldol and Friedel-Crafts Reactions

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 21, Pages 15011-15019

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01713

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Funding

  1. National Natural Science Foundation of China [21971138]

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A novel tandem synthesis of 1,3-disubstituted naphthalenes is developed using TfOH-promoted directed-aldol and Friedel-Crafts reactions. The discovery of a chemoselective directed-aldol reaction between different ketones with alpha-hydrogens enables the efficient creation of new C-C bonds and a benzene ring in one pot.
A TfOH-promoted tandem synthesis of 1,3-disubstituted naphthalenes is developed via a directed-aldol reaction and a Friedel-Crafts reaction. Two new C-C bonds and one new benzene ring are created efficiently in one pot due to the discovery of a TfOH-promoted highly chemoselective directed-aldol reaction between two different ketones with alpha-hydrogens.

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