| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 50354 | Catalysis Communications | 2015 | 5 Pages |
•A novel indium-catalyzed C–C coupling reaction is presented.•It allowed the preparation of new butadiene dyes from alkynols and indan-1,3-dione.•The process takes place in pure water under MW irradiation.•This is the first example of a Meyer–Schuster/Knoevenagel tandem process in water.
In this contribution, the high-yield preparation and optical properties of some donor-acceptor butadiene dyes, generated by coupling of different 1,1-diaryl-2-propyn-1-ols with indan-1,3-dione, are presented. The reactions, which involve the initial Meyer–Schuster rearrangement of the aromatic alkynols and subsequent condensation of the resulting enals with the β-dicarbonyl compound, proceeded cleanly in water, under MW irradiation, in the presence of catalytic amounts of the inexpensive Lewis acid InCl3. A single-crystal X-ray diffraction study of one of these dyes is also included.
Graphical abstractThe preparation of novel push-pull butadiene dyes in water, by catalytic coupling of terminal propargylic alcohols with indan-1,3-dione, is described. Inexpensive InCl3 was used as the catalyst and microwave irradiation as the heating source.Figure optionsDownload full-size imageDownload as PowerPoint slide
