An Efficient Method for the Olefination of Aldehydes with Ethyl Diazoacetate Using Iron (II) Phthalocyanine as Catalyst

Abstract

A variety of aliphatic and aromatic aldehydes were smoothly converted to the corresponding olefins in excellent yields with ethyldiazoacetate using iron (II) phthalocyanine as catalyst in the presence of triphenylphosphine as reducing agent.

Iridium Complexes in Olefination Reactions

“…Various late transition metal complexes derived from Mo, Re, Fe, Ru, and Co catalyzed the olefination of aldehydes with diazo carbonyl reagents and triphenylphosphine . These nonbasic reaction conditions allowed the synthesis of conjugated esters and ketones in high yields and excellent E -selectivity.…”

Organometallic Ruthenium Complexes: Application in the Olefination of Carbonyl Compounds

“…Furthermore, the use of transition metal complexes as catalysts also opens the possibility of efficient asymmetric olefination . Accordingly, several catalytic aldehyde and ketone olefination systems have been reported based on Ru, Re, Rh, Fe, and Co complexes.…”

Contrasting Reactivity of 2-Mesityl-1,8-Naphthyridine (Mes-NP) with Singly-Bonded [RhII–RhII] and [RuI–RuI] Compounds

“…[48] Transition-metal catalyzed olefination of aldehydes with diazoacetate in the presence of triarylphosphine has emerged as an efficient method for the construction of C¼C double bonds. [49][50][51][52][53][54][55][56][57][58] Ruthenium and rhodium complexes are well known carbene-transfer catalysts from commercially available ethyl diazoacetate (EDA). Reaction of benzaldehyde (1 mmol), triphenylphosphine (Ph 3 P, 1.2 mmol), EDA (1.5 mmol) and catalytic amount of 2 (0.01 mmol) gave ethyl cinnamate in 68% conversion after 6 h (Table 3, entry 3).…”