Open AccessMild Regiospecific Synthesis of 1-Alkoxy-isochromenes Catalyzed by Well-Defined [Silver(I)(Pyridine-Containing Ligand)] Complexes
Author(s) -
Monica Dell’Acqua,
B. Castano,
Clara Cecchini,
Tommaso Pedrazzini,
Valentina Pirovano,
Elisabetta Rossi,
Alessandro Caselli,
Giorgio Abbiati
Publication year - 2014
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/jo5002559
Subject(s) - chemistry , pyridine , regioselectivity , alkoxy group , catalysis , ligand (biochemistry) , reaction mechanism , medicinal chemistry , combinatorial chemistry , organic chemistry , polymer chemistry , alkyl , biochemistry , receptor
The synthesis of 3-substituted-1-alkoxyisochromenes starting from 2-alkynylbenzaldehydes and different alcohols is reported. The reaction is catalyzed by a silver(I) complex with an original macrocyclic pyridine-containing ligand. The approach is characterized by absolute regioselectivity, mild reaction conditions, good to excellent reaction yields, cleanness of the reaction, and reduced purification steps. The reaction mechanism was investigated by in-depth (1)H NMR experiments and an aimed "trapping" experiment.