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Synlett 2008(17): 2721-2722  
DOI: 10.1055/s-2008-1067134
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Ethyl Diazoacetate (EDA)

Gailing Liu*
College of Environmental and Chemical Engineering, Dalian University­, Dalian 116622, P. R. of China
e-Mail: liugailing1177@163.com;
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Publication History

Publication Date:
02 July 2008 (online)

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Introduction

Ethyl diazoacetate (EDA), a typical alkyl diazoacetate, is an important, commercially available reagent in organic chemistry. It is a yellow liquid, stable below 5 ˚C, and can even be kept at ambient temperature for a few days in the absence of light. Early research with this reagent using light activation was not fruitful due to the high reactivity and low selectivity of the produced carbene intermediate in the subsequent reactions. However, in the presence of catalysts, EDA can be used as a versatile carbene precursor in chemical reactions including C-H, O-H, and N-H insertion reactions, and cyclopropanation of olefins in good selectivities. Due to the acidity of the α-H, EDA can also be used in aldol-type reactions.

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