Chemistry and Biochemistry

Professor Ess Lands Front Cover of the Journal of the American Chemical Scoiety

Posted: in Faculty, Organic, Research, Jun 03, 2013

Professor Daniel Ess and colleagues earned the front cover of the Journal of the American Chemical Society (JACS) for their research on biaryl structural motifs.

The team developed several new ways to link aromatic carbon rings to make biaryls, a common structure in pharmaceuticals, biologically active natural products, and transition-metal ligands. There are a variety of ways to create this link, but these new methods are especially useful.

“The biaryl carbon-carbon link is generally difficult to achieve,” Ess said. “We wanted to find new ways to create that link.

Typically, biaryls are formed by preparing highly reactive substrates using multiple steps and then finally making the important biaryl linkage. In the first of two JACS communications, Laszlo Kurti at the University of Texas Southwestern Medical Center and Ess developed a new method that uses a single reaction to make the biaryl bond. The reaction begins by first forming a weak bond, such as N-O bond, that then undergoes a rearrangement to create the strong aryl C-C link. Importantly, the team achieved the new link without the need of transition-metal catalysts. Ess and his team here at Brigham Young University used quantum mechanics to model how and why the reaction occurs.

"This reaction provides great potential because it opens the door to several new and exciting biaryl structures that were previously unavailable or very difficult to make,” Ess explained.

In a second JACS publication, the same two research teams developed a catalytic approach to directly forming biaryl links in a single step. This new reaction is impressive because it also creates the biaryl link with so-called axial chirality.

Chemical and Engineering News recently covered both papers in an online article.

By Ellen Westenhaver, Daniel Ess