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Issue 89, 2016
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Dehydrative condensation of carbonyls with non-acidic methylenes enabled by light: synthesis of benzofurans

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Abstract

Condensation of carbonyls with non-acidic methylenes such as those adjacent to heteroatoms and allylic types to generate C[double bond, length as m-dash]C bonds is challenging but highly desirable. Inventing novel methods that can accomplish such condensations can enrich synthetic chemists' toolbox. Herein, we report a simple, clean, and high yielding protocol promoted by light to achieve condensation of non-acidic methylenes with carbonyls. As examples to demonstrate the power of this methodology, one class of ubiquitous and highly important heterocycles, i.e. benzofurans, were synthesized with broad functional group compatibility. Furthermore, intermolecular condensations were also briefly investigated.

Graphical abstract: Dehydrative condensation of carbonyls with non-acidic methylenes enabled by light: synthesis of benzofurans

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Supplementary files

Article information


Submitted
20 Sep 2016
Accepted
10 Oct 2016
First published
11 Oct 2016

Chem. Commun., 2016,52, 13120-13123
Article type
Communication

Dehydrative condensation of carbonyls with non-acidic methylenes enabled by light: synthesis of benzofurans

W. Liu, N. Chen, X. Yang, L. Li and C. Li, Chem. Commun., 2016, 52, 13120 DOI: 10.1039/C6CC07626B

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