Issue 24, 2014

Preparation of functionalized heteroaromatics using an intramolecular Wittig reaction

Abstract

The development of efficient methods for the synthesis of heteroaromatic compounds is always of great importance for chemists. In this ‘Perspective’, we describe a general approach for the synthesis of functionalized heteroaromatics via intramolecular Wittig reactions. In all cases, the reaction proceeds via in situ generated phosphorus ylides. We especially emphasize the importance of chemoselective intramolecular Wittig reactions using designed Michael acceptors and suitable acyl chloride as trapping reagents, which allows formation of two different classes of heteroaromatics from the same substrates. This metal-free approach is quite general and works in a number of examples, furnishing the corresponding products in moderate to good yields under relatively mild reaction conditions.

Graphical abstract: Preparation of functionalized heteroaromatics using an intramolecular Wittig reaction

Article information

Article type
Perspective
Submitted
28 Feb 2014
Accepted
10 Apr 2014
First published
11 Apr 2014

Org. Biomol. Chem., 2014,12, 4044-4050

Preparation of functionalized heteroaromatics using an intramolecular Wittig reaction

U. Das, Y. Tsai and W. Lin, Org. Biomol. Chem., 2014, 12, 4044 DOI: 10.1039/C4OB00464G

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