Organotin Chemistry in Cross-Coupling Reactions
Summary
Organotin reagents have occupied a pivotal role in modern synthetic methodology, most notably within Stille and related cross-coupling protocols. The unique bond polarity and reactivity of carbon–tin linkages facilitate reliable transmetallation to transition-metal centres under mild conditions, enabling the construction of diverse C–C frameworks with high functional-group tolerance. Advances in catalyst design have ameliorated traditional limitations associated with tin by-products, directing attention towards stereoselective and regioselective transformations. In particular, hydrostannylation of unsaturated substrates provides access to alkenyl and aryl stannanes that serve as versatile intermediates for coupling with aryl, vinyl and heteroaryl electrophiles. Recent efforts have concentrated on refining the selectivity of these hydrostannylation steps, developing recyclable catalyst systems and expanding stereospecific coupling of enantioenriched organostannanes. Collectively, these innovations underpin the sustained relevance of organotin chemistry in both academic and industrial settings, where complex molecule assembly and late-stage functionalisation remain paramount.
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Organotin Chemistry in Cross-Coupling Reactions publication trend
The graph below shows the total number of articles in organotin chemistry in cross-coupling reactions across all publications each year (not limited to Nature Index journals).
Technical terms
Organostannane: An organometallic compound containing at least one carbon–tin bond, used as nucleophilic coupling partner in cross-coupling.
Cross-coupling reaction: A transition metal catalysed process that joins two organic fragments by forming a new carbon–carbon bond, typically via oxidative addition, transmetallation and reductive elimination.
Hydrostannylation: The addition of a tin hydride (R₃SnH) across unsaturated bonds (alkenes or alkynes) to produce organostannane intermediates with defined regiochemistry.
Transmetallation: A key step in cross-coupling where an organic group transfers from one metal centre (such as tin) to another (such as palladium).
Stereospecificity: The property of a reaction to preserve the stereochemical configuration of a substrate in the product, crucial in enantioenriched organotin couplings.
Regioselectivity: Preference for bond formation at one position over another on an unsymmetrical substrate, determining the location of organotin incorporation.
References
- Platinum Catalysed Hydrostannylation of Terminal Alkynes; Highly Selective Synthesis of Vinyl Stannanes. Advanced Synthesis & Catalysis (2023).
- Strategies for the Controlled Hydrostannylation of Alkynes. European Journal of Organic Chemistry (2023).
- A general approach to stereospecific Pd-catalyzed cross-coupling reactions of benzylic stereocenters. Chemical Science (2023).
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