The tandem acetalization/cycloisomerization of ortho-alkynylbenzaldehydes, originally reported by Yamamoto using Pd(OAc)2 as a catalyst, gives 1H-isochromene derivatives that can have useful medicinal properties. Although several related tandem processes using different nucleophiles are known, no enantioselective version of this reaction has appeared until the very recent report by Slaughter and coworkers. Their study, published after we started our investigations, is based on the use of chiral gold(I) acyclic diaminocarbene complexes as catalysts in the presence of LiNTf2 (Tf=trifluoromethanesulfonyl) as a necessary additive to achieve useful activity. Recent studies in our research group demonstrated the efficacy of Cu(I) complexes derived from novel macrocyclic ligands containing a pyridine ring (Pc-L*) in the cyclopropanation reaction. The excellent results obtained up to now with copper prompted us to verify the application of silver(I) complexes of these ligands in catalysis. We herein report the synthesis of the new Ag(I) macrocyclic complexes, and their catalytic activity in the synthesis of oxygenated heterocycles by addition/cycloisomerization reactions of alcohols and ortho-alkynylbenzaldehydes.

Alkynylbenzaldehyde cyclizations catalyzed by Ag(I) complexes of chiral pyridine containing macroclyclic ligands (Pc-L*) / A. Caselli, G. Abbiati, B. Castano, M. Dell’Acqua, E. Gallo, E. Rossi. ((Intervento presentato al 10. convegno Co.G.I.C.O. Congresso del Gruppo Interdivisionale di Chimica Organometallica tenutosi a Padova nel 2012.

Alkynylbenzaldehyde cyclizations catalyzed by Ag(I) complexes of chiral pyridine containing macroclyclic ligands (Pc-L*)

A. Caselli
Primo
;
G. Abbiati
Secondo
;
B. Castano;M. Dell’Acqua;E. Gallo
Penultimo
;
E. Rossi
Ultimo
2012-06

Abstract

The tandem acetalization/cycloisomerization of ortho-alkynylbenzaldehydes, originally reported by Yamamoto using Pd(OAc)2 as a catalyst, gives 1H-isochromene derivatives that can have useful medicinal properties. Although several related tandem processes using different nucleophiles are known, no enantioselective version of this reaction has appeared until the very recent report by Slaughter and coworkers. Their study, published after we started our investigations, is based on the use of chiral gold(I) acyclic diaminocarbene complexes as catalysts in the presence of LiNTf2 (Tf=trifluoromethanesulfonyl) as a necessary additive to achieve useful activity. Recent studies in our research group demonstrated the efficacy of Cu(I) complexes derived from novel macrocyclic ligands containing a pyridine ring (Pc-L*) in the cyclopropanation reaction. The excellent results obtained up to now with copper prompted us to verify the application of silver(I) complexes of these ligands in catalysis. We herein report the synthesis of the new Ag(I) macrocyclic complexes, and their catalytic activity in the synthesis of oxygenated heterocycles by addition/cycloisomerization reactions of alcohols and ortho-alkynylbenzaldehydes.
catalysis; domino reaction; addition/cycloisomerization; silver; pyridine containing macrocyclic ligands; ortho-alkynylbenzaldehydes; isochromenes
Settore CHIM/03 - Chimica Generale e Inorganica
Settore CHIM/06 - Chimica Organica
Società Chimica Italiana
Università degli Studi di Padova
Gruppo Interdivisionale di Chimica Organometallica
Alkynylbenzaldehyde cyclizations catalyzed by Ag(I) complexes of chiral pyridine containing macroclyclic ligands (Pc-L*) / A. Caselli, G. Abbiati, B. Castano, M. Dell’Acqua, E. Gallo, E. Rossi. ((Intervento presentato al 10. convegno Co.G.I.C.O. Congresso del Gruppo Interdivisionale di Chimica Organometallica tenutosi a Padova nel 2012.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/202354
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