A new and efficient method for the selective olefination of aldehydes with ethyl diazoacetate catalyzed by an iron(II) porphyrin complex.

Abstract

Olefination of aromatic and aliphatic aldehydes with ethyl diazoacetate was achieved in excellent yields with triphenylphosphine and catalytic amounts of iron(II) meso-tetra(p-tolyl)porphyrin. The reaction conditions are mild and the process is efficient and highly selective (>90%) for the synthesis of the trans-olefin isomer. Results of mechanistic studies are discussed.