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Silver‐Catalysed Domino Approach to 1,3‐Dicarbo‐Substituted Isochromenes
Author(s) -
Dell'Acqua Monica,
Pirovano Valentina,
Peroni Stefano,
Tseberlidis Giorgio,
Nava Donatella,
Rossi Elisabetta,
Abbiati Giorgio
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601602
Subject(s) - chemistry , regioselectivity , trifluoromethanesulfonate , domino , cascade reaction , reaction conditions , combinatorial chemistry , cascade , catalysis , organic chemistry , chromatography
We report herein the first example of the silver triflate catalysed synthesis of 1,3‐dicarbo‐substituted isochromene derivatives starting from 2‐alkynyl(hetero)arylaldehydes and enolizable ketones. The reaction proceeds in a cascade fashion under mild heating with complete regioselectivity and moderate‐to‐good yields. In some cases, the reaction gives unexpected homodimeric products. Two competitive mechanistic paths for the formation of the desired isochromene derivatives and the homodimeric products are described.