Issue 30, 2020

Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes

Abstract

Described here is a modular strategy for the rapid synthesis of β-functionalized electron-rich naphthalenes, a family of valuable molecules lacking general access previously. Our approach employs an intermolecular benzannulation of in situ generated isobenzopyrylium ions with various electron-rich alkynes, which were not well utilized for this type of reaction before. These reactions not only feature a broad scope, complete regioselectivity, and mild conditions, but also exhibit unusual product divergence depending on the substrate substitution pattern. This divergence allows further expansion of the product diversity. Control experiments provided preliminary insights into the reaction mechanism.

Graphical abstract: Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes

Supplementary files

Article information

Article type
Edge Article
Submitted
02 May 2020
Accepted
04 Jul 2020
First published
06 Jul 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 7957-7962

Benzannulation of isobenzopyryliums with electron-rich alkynes: a modular access to β-functionalized naphthalenes

A. Wu, H. Qian, W. Zhao and J. Sun, Chem. Sci., 2020, 11, 7957 DOI: 10.1039/D0SC02502J

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