Ethyl Diazoacetate (EDA)

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Ethyl diazoacetate synthesis in flow

Ethyl diazoacetate is a versatile compound in organic chemistry and frequently used on lab scale. Its highly explosive nature, however, severely limits its use in industrial processes. The in-line coupling of microreactor synthesis and separation technology enables the synthesis of this compound in an inherently safe manner, thereby making it available on demand in sufficient quantities. Ethyl ...

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Silver-catalyzed C-C bond formation between methane and ethyl diazoacetate in supercritical CO₂.

Even in the context of hydrocarbons' general resistance to selective functionalization, methane's volatility and strong bonds pose a particular challenge. We report here that silver complexes bearing perfluorinated indazolylborate ligands catalyze the reaction of methane (CH(4)) with ethyl diazoacetate (N(2)CHCO(2)Et) to yield ethyl propionate (CH(3)CH(2)CO(2)Et). The use of supercritical carbo...

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Reactivity of 2-methylene-1,3-dicarbonyl compounds. 1,3-dipolar cycloaddition reaction with ethyl diazoacetate.

The reaction of 2-methylene-1,3-dicarbonyl compounds (1) with ethyl diazoacetate gave 4,5-dihydro-1H-pyrazole derivatives (2), which were stable for several months at room temperature in good yields.

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Direct catalytic asymmetric aldol-type reaction of aldehydes with ethyl diazoacetate.

The direct aldol-type condensation of aldehydes with ethyl diazoacetate catalyzed by the chiral complex of BINOL derivatives-Zr(O(t)Bu)(4) gave beta-hydroxy alpha-diazo carbonyl compounds with moderate enantioselectivities (53-87% ee). [reaction: see text]

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Ethyl Lithiodiazoacetate: Extremely Unstable Intermediate Handled Efficiently in Flow.

Ethyl diazoacetate (EDA) is one of the most prominent diazo reagents. It is frequently used in metal-carbene-type reactions. However, EDA can also be used as a nucleophile under base catalysis. Whilst the addition of EDA to aldehydes can be performed using organic bases, the addition of EDA to other carbonyl electrophiles requires the use of organometallics such as lithium diisopropylamide (LDA...

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ژورنال

عنوان ژورنال: Synlett

سال: 2008

ISSN: 0936-5214,1437-2096

DOI: 10.1055/s-2008-1067134