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Issue 21, 2020
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1,4-Addition of o-naphthoquinone methides induced by silver-catalyzed cyclization of enynones: an approach to unsymmetrical triarylmethanes and benzo[f]chromenes

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Abstract

The 1,4-addition reaction of ortho-naphthoquinone methide (o-NQM) intermediates induced by silver-catalyzed ring formation with electron-rich aromatic compounds and α-methylene ketones has been developed. This reaction provides an efficient method to construct versatile unsymmetrical triarylmethanes and benzo[f]chromenes under mild conditions. This transient intermediate was inseparable due to reversible dimerization but could be stored by forming a boric acid adduct for further transformations.

Graphical abstract: 1,4-Addition of o-naphthoquinone methides induced by silver-catalyzed cyclization of enynones: an approach to unsymmetrical triarylmethanes and benzo[f]chromenes

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Submitted
13 Jul 2020
Accepted
20 Sep 2020
First published
21 Sep 2020

Org. Chem. Front., 2020,7, 3387-3392
Article type
Research Article

1,4-Addition of o-naphthoquinone methides induced by silver-catalyzed cyclization of enynones: an approach to unsymmetrical triarylmethanes and benzo[f]chromenes

F. Wu, L. Zhang and S. Zhu, Org. Chem. Front., 2020, 7, 3387
DOI: 10.1039/D0QO00825G

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