The synthesis of 3-substituted-1-alkoxyisochromenes starting from 2-alkynylbenzaldehydes and different alcohols is reported. The reaction is catalysed by a silver(I)complex with an original macrocyclic pyridine-containing ligand (Pc-L). The approach is characterised by absolute regioselectivity, mild reaction conditions, good to excellent reaction yields, cleanness of the reaction and reduced purification steps. The reaction mechanism is investigated by in-depth 1H NMR experiments and an aimed “trapping” experiment.

Mild Regiospecific Synthesis of 1-Alkoxy-isochromenes Catalysed by Well-Defined [Silver(I)(Pc-L)] Complexes / M. Dell'Acqua, B. Castano, C. Cecchini, T. Pedrazzini, V. Pirovano, E. Rossi, A. Caselli, G. Abbiati. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 79:8(2014 Apr 18), pp. 3494-3505.

Mild Regiospecific Synthesis of 1-Alkoxy-isochromenes Catalysed by Well-Defined [Silver(I)(Pc-L)] Complexes

M. Dell'Acqua
Primo
;
B. Castano
Secondo
;
T. Pedrazzini;V. Pirovano;E. Rossi;A. Caselli
Penultimo
;
G. Abbiati
2014-04-18

Abstract

The synthesis of 3-substituted-1-alkoxyisochromenes starting from 2-alkynylbenzaldehydes and different alcohols is reported. The reaction is catalysed by a silver(I)complex with an original macrocyclic pyridine-containing ligand (Pc-L). The approach is characterised by absolute regioselectivity, mild reaction conditions, good to excellent reaction yields, cleanness of the reaction and reduced purification steps. The reaction mechanism is investigated by in-depth 1H NMR experiments and an aimed “trapping” experiment.
containing macrocyclic ligands; cyclic alkenyl ethers; PC-L-asterisk; electrophilic cyclization; domino reactions; asymmetric cyclopropanation; regionselective synthesis; heterocyclic synthesis; acetylenic aldehydes; organic-chemistry
Settore CHIM/06 - Chimica Organica
Settore CHIM/03 - Chimica Generale e Inorganica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/235615
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