A short desymmetrization protocol for the coordination environment in bis-salphen scaffolds |
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Authors: | Escudero-Adán Eduardo C Martínez Belmonte Marta Martin Eddy Salassa Giovanni Benet-Buchholz Jordi Kleij Arjan W |
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Institution: | Institute of Chemical Research of Catalonia (ICIQ), Av. Pai?sos Catalans 16, 43007 Tarragona, Spain. |
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Abstract: | A remarkable short preparation of desymmetrized bis-salphen scaffolds is presented. The protocol consists of an hydroxide-mediated hydrolysis of Lewis acidic bis-Zn(salphen) complexes yielding C(s)-symmetric diimine/amine salts that can be selectively transformed into bis-salphens with dissymmetric substitution patterns within each salphen unit under mild conditions. These isolated nonsymmetrical bis-salphen derivatives do not show signs of imine scrambling or decomposition due to a metal template effect. A possible rationale is provided for the formation and isolation of one of the intermediate bis-phenolate salts, and the hypothesis involves H-bond directed hydrolysis of the nearest located imine bond across the bis-salphen scaffold. |
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