New Efficient Procedures for Direct Introduction of the Agrochemically Important β-Methoxypropenoate Unit into Substituted Aromatic Derivatives

Renzo Rossi; Fabio Bellina; Adriano Carpita

doi:10.1055/s-1996-5403

Synlett 1996; 1996(4): 356-358
DOI: 10.1055/s-1996-5403

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New Efficient Procedures for Direct Introduction of the Agrochemically Important β-Methoxypropenoate Unit into Substituted Aromatic Derivatives

Renzo Rossi^* , Fabio Bellina, Adriano Carpita

^*Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Risorgimento 35, I-56126 Pisa, Italy

Abstract

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Two simple and efficient procedures for the synthesis of methyl (E)-2-aryl-3-methoxypropenoates 1 were developed. The first procedure involves a Pd-catalyzed cross-coupling reaction between arylzinc chlorides and methyl (Z)-2-iodo-3-methoxypropenoate 4. The second procedure consists in a Pd-catalyzed cross-coupling reaction between arylboronic acid and methyl (Z)-2-bromo-3-methoxypropenoate 6. This electrophile has been prepared by Pd-catalyzed reaction of methyl (Z)-2,3-dibromopropenoate 7 with Bu₃SnOMe. Other unprecedented regioselective carbon-oxygen bond and carbon-sulfur bond forming reactions occurred when 7 or its stereoisomer was reacted with alkoxy- and arylthio- or alkylthio-tributylstannanes, respectively, in the presence of Pd(PPh₃)₄.

palladium-catalyzed carbon-carbon bond - carbon-oxygen bond and carbon-sulfur bond forming reactions

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