Journal of Organic Chemistry p. 3494 - 3505 (2014)
Update date:2022-08-02
Topics:
Dellacqua, Monica
Castano, Brunilde
Cecchini, Clara
Pedrazzini, Tommaso
Pirovano, Valentina
Rossi, Elisabetta
Caselli, Alessandro
Abbiati, Giorgio
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 1H NMR experiments and an aimed trapping experiment.
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Doi:10.1021/ol5008179
(2014)Doi:10.1039/P19940001275
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(1980)