Research Projects

Organoboron compounds play a crucial role in synthetic organic chemistry, offering immense versatility and value in areas such as total synthesis, complex molecule construction, the production of API chemicals, facilitating late-stage molecular editing in drug modification, and various industrial applications. Given their widespread applications, organoboron compounds are synthesized through various methods, including the use of organometallic reagents or transition metal-catalyzed systems. However, a significant drawback of transition metal-catalyzed procedures is the reliance on precious metals such as Pd, Rh, and Ir, which also produce undesirable metal-containing residues as contaminants, limiting the practical use of these methods. In contrast, using main group compounds instead of transition metals is an attractive alternative. Main group compounds are generally more cost-effective, easier to handle, and composed of Earth-abundant elements, providing distinct advantages over transition metal catalysts. Recent trends have shifted towards using electrophilic main group reagents (such as B electrophiles) to synthesize organoborane compounds via electrophilic substitution. This approach addresses several issues, including cost-effectiveness, ease of handling, high substrate tolerance, scalability, and applicability in industrial settings. This proposal aims to design and synthesize bis-borane ditopic electrophiles to tackle key challenges in organoboron chemistry. Specifically, we address the following issues: (1) Metal-free electrophilic borylation protocols:- Current metal-free borylation methods are limited, especially for electron-deficient systems. Considering this, we propose to innovate a super boron electrophile that enables efficient electrophilic borylation across a broad range of substrates, regardless of their electronic properties. (2) Double arene C–H borylation for 1,2-difunctionalized isomers:- Metal-catalyzed methods for synthesizing 1,2-difunctionalized isomers via double arene C–H borylation are challenging. This issue will be addressed by utilizing ditopic boron electrophiles to enable selective double functionalization. (3) Synthesis of oxaboroles as bioactives:- With the growing interest in oxaboroles as bioactive compounds, we propose a one-step, scalable synthetic route to prepare oxaboroles by selectively activating C–H bonds. This method is particularly relevant for drug synthesis and modification, allowing for the introduction of boron-functionalities at the late stage of synthesis to minimize the risk of decomposition. By addressing these challenges, this project aims to contribute valuable new methods to both synthetic and medicinal chemistry, with the potential for significant impact on drug development and modification. The outcomes of this research will undoubtedly advance the field of organoboron chemistry, offering more efficient, scalable, and sustainable strategies for a wide range of applications.