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Organotin Reagents

A sample of our organotin compound portfolio featuring allyltriphenylstannane, dibutyltin maleate, and tributyltin chloride

Organotin reagents are pivotal in progressing organic synthesis in the quest for synthesizing highly complex natural compounds and creating new chemical structures and known bond formations.  Organotin compounds, also known as stannanes, have at least one tin-carbon bond and are frequently utilized synthons in palladium-catalyzed cross coupling reactions. Since the first report by Stille in 1977, numerous applications of organotin reagents have become commonplace in the formation of new carbon-carbon (C-C) bonds for the synthesis of natural products and other small molecules for drug discovery.   

Organotin chemistry continues to be an active field of research in organometallic chemistry and has a wide range of pharmacological, agrochemical, and polymerization applications. Our organotin reagents are used for the generation of Stille Coupling precursors to obtain more complex coupling partners and dehalogenation reactions to afford hydrocarbons in late-stage synthetic sequences. 

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Our extensive portfolio of organotin compounds includes:

  • Organotin halides
  • Organotin hydrides
  • Organotin oxides and hydroxides
  • Hypercoordinated stannanes
  • Triorganotin salts

We also offer other organometallic reagents to facilitate cross-coupling reactions and the discovery of new bond-forming methodologies. To view these reagents, visit our Organolithium, Organozinc, Organoaluminum, and Organosilicon reagents pages.

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Our offering organotin reagents and compounds are useful in the formation of known bond formations and the development of new technologies in organic synthesis.
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.
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