MilliporeSigma

Organozinc Reagents

Common organic reactions using organozinc reagents

Organozinc reagents, first prepared by Frankland in 1848, are used extensively in organic synthesis as powerful C–C bond-forming tools, participating in Cu(I)-promoted reactions (developed at Rieke Metals, Inc.) or in Pd-catalyzed cross-coupling reactions (i.e. the Negishi coupling), as well as Michael additions, and electrophilic amination reactions. Interestingly, the choice of preparative route to organozinc reagents of the type RZnX (R=alkyl, aryl; X=halide) plays an important role in the reactivity and stability of these compounds.  

We offer a comprehensive range of organozinc compounds, including Rieke® Organozinc Reagents that are stable as solutions in tetrahydrofuran, Rieke® Zinc, as well as numerous pre-formed Rieke® organozinc reagents. Prior to the discovery of Rieke® Zinc, it was not possible to react alkyl, aryl, and vinyl bromides or chlorides directly with zinc metal. The preparation of these reagents was only possible by a metathesis reaction of a zinc halide with an organolithium or Grignard reagent. Unfortunately, this approach was of limited utility since the process was not compatible with many types of functional groups. Rieke® Zinc, on the other hand, will react directly with the bromides or chlorides and will tolerate a variety of sensitive groups such as nitriles, esters, amides, ethers, sulfides, and ketones to give functionalized organozinc reagents. 

Read more



Since many organozinc reagents are pyrophoric, we provide top-quality packaging in Sure/Seal bottles to prolong the lifetime of these reagents. A growing list of organometallic reagents are also being transitioned into exclusive 25 mL Sure/Seal packaging to reduce waste and decomposition of more unstable organometallic reagents, by requiring fewer needle entries to consume the reagent volume.

Face your cross-coupling challenges with our reliable range of organozinc reagents to keep your focus on creating breakthroughs.


Related Resources

  • Rieke® Highly Reactive Metals

    Metal-enhanced organic synthesis via organometallic intermediates is a widely used preparative route for thousands of organic compounds.

  • Tech Bulletin: Handling Pyrophoric Reagents

    Due to the hazardous nature of pyrophoric reagents, we strongly recommend that all users read this bulletin carefully and completely before starting any actual laboratory work.




Sign In To Continue

To continue reading please sign in or create an account.

Don't Have An Account?