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Easy entry to donor/acceptor butadiene dyes through a MW-assisted InCl3-catalyzed coupling of propargylic alcohols with indan-1,3-dione in water

Paper ID Volume ID Publish Year Pages File Format Full-Text
50354 46792 2015 5 PDF Available
Title
Easy entry to donor/acceptor butadiene dyes through a MW-assisted InCl3-catalyzed coupling of propargylic alcohols with indan-1,3-dione in water
Abstract

•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

Keywords
Homogeneous catalysis; Aqueous catalysis; Indium trichloride; Meyer–Schuster rearrangement; C–C couplings; Butadiene dyes
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Easy entry to donor/acceptor butadiene dyes through a MW-assisted InCl3-catalyzed coupling of propargylic alcohols with indan-1,3-dione in water
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 63, 10 March 2015, Pages 10–14
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us