Facile Utilisation of Aldehyde Bisulfite Adducts: Synthesis of (E)-1,2- Diphenylethenes

Author(s): K. P. Vinay Kumar , C. Jaganmohan , G. Sandeep Reddy , Sandeep Mohanty , Jaydeep Kumar , Venkateswara Rao .

Journal Name: Letters in Organic Chemistry

Volume 14 , Issue 2 , 2017

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Abstract:

Background: A one-pot coupling reaction of aldehyde bisulfite adducts was developed for McMurry reaction using Zn-TiCl4 in 1,4-dioxane solvent medium. The treatment of sodium hydroxy( phenyl)methane sulfonate (2a) with TiCl4 in 1,4-dioxane favoured the deprotection of the bisulfite adduct 2a, and the in situ regeneration of benzaldehyde (1a) underwent reductive coupling to afford stilbene 3a in a relatively good yield, thus leading to an improved synthesis of a series of (E)-1,2- diphenylethenes 3. The present approach provides a new solution to the inherent instability of aldehydes and also provides a direct access to C–C bond formation for the synthesis of 1,2-diphenylethenes from aryl aldehyde bisulfite adducts.

Methods: All reactions were performed at 70-80o and the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectrometric techniques.

Results: The present approach provides a new solution to the instability of aldehydes and also provides a direct access to C–C bond formation for the synthesis of 1,2-diphenylethenes from aryl aldehyde bisulfite adducts.

Conclusion: In the present work, we have reported an efficient method for the synthesis of 1,2- diphenylethene derivatives. Aldehydes are commonly used as the starting materials in the McMurry reaction, which affords the stilbene derivatives, the core skeleton of various valuable compounds. To increase the stability of the aldehydes, bisulfite adducts are usually employed, but the deprotection process causes loss of process efficiency. To address this issue, we developed a method based on the single-pot reaction of aromatic bisulfite adduct using TiCl4/Zn in 1,4-dioxane.

Keywords: Aromatic aldehyde, bisulfite adduct, 1, 4-dioxane, stilbene, TiCl4, Zn dust.

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Article Details

VOLUME: 14
ISSUE: 2
Year: 2017
Page: [109 - 114]
Pages: 6
DOI: 10.2174/1570178614666170203095116
Price: $58

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