Diboration Techniques in Organic Synthesis
Summary
Diboration techniques involve the introduction of two boron atoms across unsaturated carbon–carbon bonds, providing a direct route to versatile organoboron intermediates with excellent atom economy. Traditional approaches have relied on transition-metal catalysts—such as palladium, platinum and copper—to activate diboron reagents (notably bis(pinacolato)diboron), effecting stereoselective and regioselective additions to alkynes, alkenes and allenes. These methods yield syn-1,2-diborylalkenes, 1,1-diborylalkenes and chiral boronic esters, which serve as pivotal building blocks in synthesis. Recent trends include metal-free protocols that employ Lewis bases or organic catalysts to generate nucleophilic boryl species under mild conditions, enhancing functional-group tolerance and reducing environmental impact.
The true strength of diboration lies in the downstream elaboration of C–B bonds. Strategic cross-coupling, oxidation and homologation of boronate esters enable rapid assembly of complex architectures, underpinning applications in medicinal chemistry, agrochemicals and advanced materials. The design of unsymmetrical diboron reagents and mixed diboration sequences offers precise control over chemo- and regioselectivity, as well as orthogonal protection patterns. Ongoing research focuses on catalyst innovation, expanded substrate scope and tandem processes that integrate diboration with subsequent transformations, thereby fostering more sustainable and efficient synthetic routes.
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Diboration Techniques in Organic Synthesis publication trend
The graph below shows the total number of articles in diboration techniques in organic synthesis across all publications each year (not limited to Nature Index journals).
Technical terms
Diboration: Addition of two boron atoms across a multiple bond, typically an alkene or alkyne.
Diboron reagent: A molecule bearing two boron centres (e.g. bis(pinacolato)diboron) used as borylating agent.
Regioselectivity: Preference for reaction at one site over another within a molecule.
Stereoselectivity: Preference for formation of one stereoisomer over another.
Catalyst: Substance that accelerates a reaction without being consumed, often improving selectivity.
References
- Enantioselective Copper-Catalyzed sp2/sp3 Diborylation of 1‑Chloro-1-Trifluoromethylalkenes. ACS Central Science (2022).
- Regio‐ and Stereoselective Synthesis of 1,1‐Diborylalkenes via Brønsted Base‐Catalyzed Mixed Diboration of Alkynyl Esters and Amides with BpinBdan. European Journal of Organic Chemistry (2020).
- Unsymmetrical Diboron Reagents: Application in Borylation Reactions of Unsaturated Bonds. Molecules (2019).
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