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Issue 37, 2019

Reversal of reaction type selectivity by Lewis acid coordination: the ortho photocycloaddition of 1- and 2-naphthaldehyde

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Abstract

The value of a specific substrate class for synthetic applications is greatly enhanced if different types of reactions can be performed selectively upon a judicious choice of reaction conditions. In the present study it was shown that the typical photochemical behaviour of naphthaldehydes is completely altered in the presence of Lewis acids. Without Lewis acids, reactions at the carbonyl group are exclusively observed while Lewis acids facilitate a visible light-mediated cycloaddition at the arene core providing access to products of aromatic C–H functionalization via cyclobutane intermediates.

Graphical abstract: Reversal of reaction type selectivity by Lewis acid coordination: the ortho photocycloaddition of 1- and 2-naphthaldehyde

Supplementary files

Article information


Submitted
04 Jul 2019
Accepted
26 Jul 2019
First published
29 Jul 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 8566-8570
Article type
Edge Article

Reversal of reaction type selectivity by Lewis acid coordination: the ortho photocycloaddition of 1- and 2-naphthaldehyde

S. Stegbauer, N. Jeremias, C. Jandl and T. Bach, Chem. Sci., 2019, 10, 8566 DOI: 10.1039/C9SC03315G

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