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Mild Regiospecific Synthesis of 1-Alkoxy-isochromenes Catalyzed by Well-Defined [Silver(I)(Pyridine-Containing Ligand)] Complexes

Monica Dell'Acqua, Brunilde Castano, Clara Cecchini, Tommaso Pedrazzini, Valentina Pirovano, Elisabetta Rossi, Alessandro Caselli* and Giorgio Abbiati*

*Dipartimento di Scienze Farmaceutiche and Dipartimento di Chimica, Università degli Studi di Milano, Via Venezian, 21, 20133 Milano, Italy, Email: giorgio.abbiatiunimi.it, alessandro.caselliunimi.it

M. Dell'Acqua, B. Castano, C. Cecchini, T. Pedrazzini, V. Pirovano, E. Rossi, A. Caseli, G. Abbiati, J. Org. Chem., 2014, 79, 3494-3505.

DOI: 10.1021/jo5002559


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Abstract

A synthesis of 3-substituted-1-alkoxyisochromenes starting from 2-alkynylbenzaldehydes and different alcohols is catalyzed by a silver(I) complex with an original macrocyclic pyridine-containing ligand. The convenient approach is characterized by absolute regioselectivity, mild reaction conditions and good to excellent reaction yields.

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Key Words

Isochromenes


ID: J42-Y2014