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Issue 41, 2018

Synthesis of perinaphthenones through rhodium-catalyzed dehydrative annulation of 1-naphthoic acids with alkynes

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Abstract

An efficient approach to the synthesis of perinaphthenones via the rhodium-catalyzed dehydrative annulation of 1-naphthoic acids with internal alkynes was developed. Norbornadiene can act as an acetylene equivalent to give unsubstituted perinaphthenones at the 2- and 3-positions via dehydrative annulation followed by a retro Diels–Alder reaction.

Graphical abstract: Synthesis of perinaphthenones through rhodium-catalyzed dehydrative annulation of 1-naphthoic acids with alkynes

Supplementary files

Article information


Submitted
20 Jun 2018
Accepted
04 Oct 2018
First published
05 Oct 2018

Org. Biomol. Chem., 2018,16, 7583-7587
Article type
Communication

Synthesis of perinaphthenones through rhodium-catalyzed dehydrative annulation of 1-naphthoic acids with alkynes

T. Fukuyama, T. Sugimori, S. Maetani and I. Ryu, Org. Biomol. Chem., 2018, 16, 7583 DOI: 10.1039/C8OB01453A

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