A team of scientists from the University of Ottawa has developed an innovative technique for preparing complex chemical structures from readily available substrates, making it one of the simplest and most practical methods for converting alcohols into their arylated equivalents.
This innovative method to carry out the reaction, namely the deoxygenative Suzuki-Miyaura arylation of aliphatic alcohols, uses two different metal catalysts. Their reaction proceeds under mild reaction conditions with minimal waste products and is expected to have a significant impact on the formation of new molecules. As a result, it will contribute to advances in the pharmaceutical, agrochemical and related industries.
This research was conducted at the University of Ottawa’s Newman LabNortheastexternal link led by Professor Stephen G. Newman, an Associate Professor of Chemistry and Biomolecular Sciences in the Faculty of Science, who holds a Canadian Tier 2 Research Chair in Sustainable Catalysis. The study’s lead author was Adam Cook, a fifth-year graduate student, and the second author was Piers St Onge, a third-year graduate student.
“The chemical reaction we developed, making full use of the high-throughput laboratories at uOttawa’s Center for Catalysis Research and Innovation, overcomes previous limitations of Suzuki-Miyaura arylation by providing a surprisingly simple method to perform the direct derivatization of a broad spectrum reach of easily accessible alcohols. By using these molecules as starting materials instead of more established organohalides, this process produces water as a waste product instead of metal halide salts. This reaction not only provides an effective method for generating complex, medically relevant structures from accessible materials, but also contributes to fundamental developments in how chemical precursors can be directly converted into important materials through catalysis,” explains Cook.
Current methods for the Suzuki–Miyaura arylation, one of the most widely used chemical reactions in the world, require multiple synthetic steps to obtain the necessary starting materials. By developing a method that makes it possible to use naturally abundant alcohols directly in these transformations, “we eliminate the need for these wasteful and time-consuming synthetic steps, thereby streamlining the process of converting naturally occurring substances into value-added products. In addition, we were able to test a unique mechanistic hypothesis towards this goal through cross-coupling reactions via a SN1-way,” says Cook.
This is an underexplored topic in synthetic chemistry, and the research team hopes that their work will serve as valuable inspiration for all scientists. “No matter how ‘flaky’ your hypothesis, high-throughput experiments can help you reach conclusions quickly and comprehensively,” concludes Cook.
By harnessing the power of this new technique, scientists can now produce a wide range of arylated alcohols with greater efficiency and precision than ever before.
The study entitled Suzuki-Miyaura deoxygenative arylation of tertiary alcohols by silyl ethersNortheastexternal link , was published in natural synthesis.
subject of research
Deoxygenative Suzuki–Miyaura arylation of tertiary alcohols by silyl ethers
Article publication date
April 20, 2023
Disclaimer: AAAS and EurekAlert! are not responsible for the accuracy of the press releases published on EurekAlert! by contributing institutions or for the use of information about the EurekAlert system.