Wadsworth–Emmons reaction: the unique catalytic reaction by a solid base

• Published in: Journal of catalysis 2003-08, Vol.218 (1), p.191-200
• Main Authors: Choudary, Boyapati M, Kantam, Mannepalli L, Reddy, Chinta Reddy V, Bharathi, Balagam, Figueras, Francois
• Format: Article
• Language: English
• Subjects: Catalysis; Catalytic reactions; Chemical Sciences; Chemistry; Exact sciences and technology; General and physical chemistry; Hydrotalcite; Potassium t-butoxide; Solid bases; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Wadsworth–Emmons reaction
• ISSN: 0021-9517; 1090-2694
• DOI: 10.1016/S0021-9517(03)00080-0

The near-stoichiometric amount of bases is used both in laboratory and industry in Wadsworth–Emmons (WE) reactions, since the by-product, (EtO) 2P(O)OH, formed in the reaction neutralizes the base into an inert salt. A strategy to design, develop, and evolve the recyclable Mg–Al–hydrotalcite–O t Bu (HT–O t Bu) by the interaction of KO t Bu with the calcined hydrotalcite that transforms a well-defined stoichiometric WE reaction into a catalytic one in an effort to minimize the quantum of effluents released and reduce the cost of the process is described here. HT–O t Bu is found to be an efficient solid base for WE reactions for the simple synthesis of α, β-unsaturated esters and nitriles for the first time. The HT–O t Bu, composed of various ratios of Mg/Al (i.e., 2, 2.5, and 3) and different contents of t BuO − (Mg/Al:3), and their precursors were prepared and well characterized to draw a correlation between structure and reactivity of the hydrotalcites in WE reactions.