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Several modifications of alkynylation reactions are known: In the Arens–van Dorp synthesis the compound ethoxyacetylene [7] is converted to a Grignard reagent and reacted with a ketone, the reaction product is a propargyl alcohol.
This alkynylation reaction is enantioselective and involves an alkynylzinc reagent [1] rather than the sodium acetylide used by John Ulric Nef in his 1899 report of the synthetic approach. [ 2 ] [ 3 ] Propargyl alcohols are versatile precursors for the chirally-selective synthesis of natural products and pharmaceutical agents , making this ...
The Cadiot–Chodkiewicz coupling in organic chemistry is a coupling reaction between a terminal alkyne and a haloalkyne catalyzed by a copper(I) salt such as copper(I) bromide and an amine base. [ 1 ] [ 2 ] The reaction product is a 1,3-diyne or di- alkyne .
English: Diagram showing the chemical reaction involving Sonogashira reaction of a phenylalanine derivative with an alkyne. Modified from File:Alkynylation.gif to correct chemical errors. Date
The alkynylation reaction of aryl halides using aromatic acetylenes was reported in 1975 in three independent contributions by Cassar, [4] Dieck and Heck [5] as well as Sonogashira, Tohda and Hagihara. [6] All of the reactions employ palladium catalysts to afford the same reaction products.
The alkyne zipper reaction is an organic reaction that involves isomerization of a non terminal alkyne into a terminal alkyne. This reaction was first reported by Alexey Favorsky in 1887 (J. Russ. Phys.-Chem. Soc., 19, 414 (1887)). Also, this reaction was reported by Charles Allen Brown and Ayako Yamashita in 1975. [1]
The reaction proceeds through generation of an acylium center. The reaction is completed by deprotonation of the arenium ion by AlCl 4 −, regenerating the AlCl 3 catalyst. However, in contrast to the truly catalytic alkylation reaction, the formed ketone is a moderate Lewis base, which forms a complex with the strong Lewis acid aluminum ...
The Corey–Fuchs reaction, also known as the Ramirez–Corey–Fuchs reaction, is a series of chemical reactions designed to transform an aldehyde into an alkyne. [1] [2] [3] The formation of the 1,1-dibromoolefins via phosphine-dibromomethylenes was originally discovered by Desai, McKelvie and Ramirez. [4]