Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach - Archive ouverte HAL
Article Dans Une Revue Journal of Organic Chemistry Année : 2009

Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach

Résumé

A straightforward and traceless solid-phase methodology was developed for the synthesis of isocoumarins. This two-step process involves a Sonogashira cross-coupling reaction between polymer-bound 2-bromobenzoates and terminal alkynes, followed by an electrophile-induced halocyclization of the resulting 2-(alk-1-ynyl)benzoates through activation of the triple bond with the subsequent release of the 3-substituted 4-haloisocoumarins. This polymer-bound parallel synthetic approach allowed us to achieve large diversity in good to excellent yields and purities.

Domaines

Chimie organique
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Dates et versions

hal-00411596 , version 1 (28-08-2009)

Identifiants

Citer

Marine Peuchmaur, Vincent Lisowski, Céline Gandreuil, Ludovic T. Maillard, Jean Martinez, et al.. Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach. Journal of Organic Chemistry, 2009, 74, pp.4158-4165. ⟨10.1021/jo900281a⟩. ⟨hal-00411596⟩
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