Novel approach in organic chemistry enables boron to be added to molecules with high precision
A major goal in organic synthesis is to develop efficient reactions to convert feedstock chemicals (otherwise known as raw or natural materials) into valuable reagents that can be used to create pharmaceuticals and agrochemicals.
A powerful approach to this core scientific challenge is to convert carbon–hydrogen bonds into carbon–heteroatom bonds. However, organic molecules are composed of a "sea" of carbon–hydrogen bonds, making it very difficult to achieve high selectivity for reaction at a specific bond.
To add another layer of difficulty, carbon–hydrogen bonds are generally unreactive, which means that harsh reaction conditions are required, often using high temperatures and expensive precious metal catalysts.
Now, scientists at the University of Bristol have discovered a mechanistically unique approach to facilitate this process in a way that is more efficient and less costly than traditional methods.
Their findings, as reported in the journal Nature today open up new possibilities for converting feedstock chemicals into valuable boron-containing compounds, which play a major role in the manufacture of numerous products, from medicines to TV screens.
This latest study, led by Professor Varinder Aggarwal FRS and Dr. Adam Noble from the School of Chemistry, describes how a process known as C–H borylation can be used to convert carbon–hydrogen bonds of organic molecules into carbon–boron bonds, which are some of the most versatile in chemical synthesis.
"An important feature of this new C–H borylation is that, unlike all previously reported methods, these reactions proceed at ambient temperature and do not require a metal catalyst, which can significantly reduce their cost," says Professor Aggarwal.
The study involved using a simple chloride catalyst in place of precious metals.Key to the success of the reaction was the use of violet-light irradiation, which provides the chloride catalyst with enough energy to break unreactive carbon–hydrogen bonds.
"Crucially, the mild reaction conditions of this photo-induced C–H borylation enable a laser-like precision as to which of the myriad of C–H bonds is transformed. In addition, since the mechanism is distinct from those that use metal catalysts, this new method allows the synthesis of boron-containing organic molecules that cannot be accessed using existing approaches, thus generating new opportunities for the synthesis of these valuable compounds from feedstock chemicals."
More information: Chao Shu et al. Metal-free photoinduced C(sp3)–H borylation of alkanes, Nature (2020). DOI: 10.1038/s41586-020-2831-6
Journal information: Nature
Provided by University of Bristol