Chemists have found a way to build stubborn four-substituted alkenes—molecules that are key components in many drugs, agrochemicals, and advanced materials—using cheap, simple starting materials and a boron-based chemical trick. The problem is that standard methods for making alkenes work well when the carbon-carbon double bond has one, two, or three non-hydrogen attachments, but they often fail when all four positions are occupied. The crowded structure makes the molecule less reactive and harder to control. This project uses tetracoordinate boron complexes, derived from inexpensive building blocks, that rearrange when an electrophile is added, producing the desired tetrasubstituted alkene with precise control over its geometry. If successful, the method could give synthetic chemists a reliable, stereoselective route to a class of molecules that has been difficult to access. That could accelerate the development of new pharmaceuticals, catalysts, and functional materials. This is fundamental science—it does not promise an immediate product—but past advances in organoboron chemistry have led to widely used reactions such as the Suzuki coupling, which transformed how pharmaceutical companies build complex molecules.
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Synthesis plays a central role in accessing new chemical spaces to expand the frontiers of chemical discovery and invention. Through careful design and execution of chemical reactions, chemists can develop novel compounds that may not exist in nature or have never been synthesized. This process enables the creation of diverse functional materials (catalysts, pharmaceuticals, agrochemicals, polymers, and more) with unique properties and applications, paving the way for scientific advancements and technological breakthroughs. Within this field, alkenes are common motifs found in natural products, pharmaceuticals, agrochemicals and advanced materials, as well as acting as ideal building blocks in synthesis. They can have anywhere between 1-4 non-hydrogen substituents and can adopt either E or Z geometry. The nature of the substituents and the geometry of the alkene are key elements which determine the molecule’s properties. Whilst numerous methods exist for constructing alkenes with 1-3 non-hydrogen substituents, methods for constructing alkenes with four substituents are much more challenging since the alkene is more hindered, reducing reactivity and it is much harder to control geometry since the steric difference between substituents is much smaller when none of them are hydrogen. Indeed, classic olefination methodologies that are well-suited for di- and trisubstituted alkenes often fail when applied to the synthesis of tetrasubstituted alkenes. This project aims to address the challenges in the synthesis of tetrasubstituted alkenes by using reactions of tetracoordinate boron complexes with electrophiles. The tetracoordinate boron complexes are derived from simple, readily available, low cost building blocks . Following addition of an electrophile, molecular rearrangement occurs leading to a tetrasubstituted alkene with control of double bond geometry. This new method will lead to improved understanding of the chemistry of tetracoordinate boron complexes, and will provide a transformative approach for the stereoselective synthesis of tetrasubstituted alkenes from simple feedstocks.
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