organocopper reagents in organic synthesis


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  • The first organocopper compound, the explosive copper(I) acetylide Cu 2C 2 ( Cu−C≡C−Cu), was synthesized by Rudolf Christian Böttger in 1859 by passing acetylene gas through a solution of copper(I) chloride: C 2H 2 + 2 CuCl → Cu 2C 2 + 2 HCl.

  • What is organocopper used for in organic synthesis?

    Finally, synthetic applications of the organocopper alkyne addition reaction are described with emphasis on the use of double acetylene carbocupration for the stereospecific preparation of Z,Z-dienes.
    The use of this methodology for the synthesis of the Navel Orangeworm pheromone is discussed.

  • How are organocopper reagents prepared?

    Generally, organocopper compounds can be prepared by transmetallation between copper salts and organometallic reagents such as RLi, RMgX, and RZnX.
    Copper alkynides can be obtained by reaction of terminal alkynes with a copper salt in the presence of a base.

  • How many types of reactions are given by organocopper reagents?

    There are three principal reactions where the organocopper species are more effective than their precursor organolithium or organomagnesium reagents: conjugate addition to a,b-unsaturated carbonyl compounds, coupling with alkyl halides, epoxides or tosylates, and carbometalation of acetylenes.

  • Reactions of organocopper reagents involve species containing copper-carbon bonds acting as nucleophiles in the presence of organic electrophiles. Organocopper reagents are now commonly used in organic synthesis as mild, selective nucleophiles for substitution and conjugate addition reactions.
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