Skip to Content
MilliporeSigma
HomeProductsChemistry & BiochemicalsChemical SynthesisOrganozinc Reagents

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 Product Resources

Article: Rieke® Highly Reactive Metals
Tech Bulletin: Handling Pyrophoric Reagents

Related Product Categories
Organoaluminum Reagents
Explore our organoaluminum reagents to enable your cross-coupling reactions and facilitate the discovery of new bond-forming methodologies.
Organosilicon Reagents
Our unprecedented portfolio of organosilicon reagents includes disilanes, silanols, silazanes, silicates, siloxanes, trialkoxysilanes to support all of your breakthrough ideas.
Grignard Reagents
Our unparalleled portfolio of Grignard Reagents are used in reactions such as Grignard reaction to form a new carbon-carbon bond.
Related Applications
C–H Functionalization
C–H functionalization is the reliable and predictable conversion of a C–H into a C–C, C–N, C–O, or C–X bond in a selective and controlled fashion.
Cross-Coupling
Cross-coupling is a common reaction in organic chemistry for the creation of C-C, C-N, and C-O bonds with the aid of a metal catalyst.
Fluorination
Fluorination is the introduction of fluorine to a compound via electrophilic fluorination, nucleophilic fluorination, difluoromethylation, trifluoromethylation, or perfluoroalkylation.
Metathesis
Olefin metathesis involves an organic reaction that redistributes fragments of alkenes (olefins) by cleavage and transformation of carbon-carbon double bonds.
Photocatalysis
Photoredox catalysis utilizes photocatalysts in the presence of visible light to form an array of synthetic transformations including, but not limited to, cross-coupling, C-H functionalization, alkene and arene functionalization, and trifluoromethylation.
Organic Reaction Toolbox
An organic reaction toolbox provides structure-activity relationships for unique chemical reactions to optimally design and control small molecule synthesis.
Related Services
SYNTHIA™ Retrosynthesis Software
Our custom cell culture product design experts can offer advice and support as you scale your bioprocess from clinical to commercial supply, assisting with liquid products, dry powder products, selection of raw materials, quality testing, flexible product packaging, and product documentation.
Sign In To Continue

To continue reading please sign in or create an account.

Don't Have An Account?