New Catalyst Developed by CCHF

Side view of the new catalyst. Graphic image by Kuangbiao Liao via escienceommons.

Chemists have developed another catalyst that can selectively activate a carbon-hydrogen bond, part of an ongoing strategy to revolutionize the field of organic synthesis and open up new chemical space.

The journal Nature is publishing the work by chemists at Emory University, following on their development of a similar catalyst last year. Both of the catalysts are able to selectively functionalize the unreactive carbon-hydrogen (C-H) bonds of an alkane without using a directing group, while also maintaining virtually full control of site selectivity and the three-dimensional shape of the molecules produced.

Read the full story by Carol Clark on the Emory esciencecommons blog!

Emory Chemistry at NOBCChE

Emory was well represented at the National Organization for Black Chemists and Chemical Engineers Conference (NOBCChE) last week.

Wallace Derricotte (Graduate Student, Evangelista Group) gave a research talk and received the ACS “Graduate Student Exchange Award” at NOBCChE. The award is a joint program between the American Chemical Society and other chemistry related organizations to provide students of these satellite organizations with travel funds for ACS national and regional conferences.

Keon Reid (Graduate Student, Kindt Group) received a NOBCChE conference award, the “Advancing Science Travel Grant.” The award covers registration and hotel costs for the conference and is intended to encourage graduate students and postdocs to attend NOBCChE in recognition of the integral contributions they make to the conference community. Keon also gave an excellent poster presentation at the conference.

Congratulations, Wallace and Keon!

Additionally, Felicia Fullilove, an Emory Alum of both the Davies and MacBeth groups, served as a speaker on a professional development talk.

Monya Ruffin, Senior Scientist and Director of Community, Diversity, and Outreach in the CCHF Center at Emory, gave a professional development talk on science communication.

Collaborative study in Nature Communications Explores Recent Advances by Emory Scientists and International Colleagues

A recent study published in Nature Communications stems from an international collaboration between scientists in Emory’s own NSF Center for Selective C-H Functionalization and the Institute of Transformative Bio-Molecules (ITbM) at Nayoga University, Japan. The article “Decarbonylative organoboron cross-coupling of esters by nickel catalysis” details work that expands the scope of a Nobel Prize-winning carbon-carbon bond reaction. The expanded reaction uses aromatic esters and boronic acids as coupling partners in the presence of a nickel catalyst. The nickel catalyst is economically and environmentally friendly, making it strategically useful for pharmaceutical, agro-chemical, and organic materials applications.

The new research builds on the 2010 Nobel prize-winning Suzuki-Miyaura cross-coupling reaction, an extremely powerful strategy to synthesize a variety of significant organic compounds on an industrial scale. The reaction is usually catalyzed by a pallidium catalyst to couple boronic acids with organic hallides. The result is extremely powerful but its reaction partners can generate corrosive waste byproducts.

Researchers at ITbM and CCHF have demonstrated that readily available esters–carbonyl compounds found in fat and oils–can be used as alternative coupling partners, generating useful products such as derivatives of plant metabolites and a drug for treating hypertension, telmisartan.

Esters are known for their distinctive odors, such as banana and pineapple, thus making them a popular ingredient in perfumes. Due to their high commercial and synthetic accessibility, the use of esters to couple with boronic acids greatly expands the scope of available substrates for the Suzuki-Miyaura cross-coupling reaction.

Theoretical calculations conducted by Professor Djamaladdin Musaev, Director of the Emerson Center at Emory University, contributed valuable insight to the mechanism of the decarbonylative cross-coupling reaction between aromatic esters and boronic acids.

“This is a beautiful work in the frontier of organic transformations,” said Musaev. “I am grateful to Professor Itami and the entire ITbM team for providing the opportunity for us to contribute to this novel research project.”

In turn, Professor Ken Itami of ITbM praises Musaev for elucidating the unusual decarbonylative cross-coupling reaction. “This is obviously a result of the strong collaboration between ITbM and CCHF. We will continue to work together to conduct further optimization of the reaction system to expand its scope.”

Itami and his colleagues envisage that ongoing advances in this reaction method may lead to the development of new industrial processes for making biologically and structurally active compounds, including aliphatic esters.

Huw Davies elected to National Academy of Inventors

Chemistry professor Huw Davies–who holds 23 patents and has published 280 scientific article–was elected to the National Academy of Inventors. Dr. Davies’ current work is focused on the design of new catalysts to enable synthetic technologies for drug discovery. He is the Director of the Center for Selective C-H Functionalization.

Dr. Davies is the director of the Center for C-H Functionalization. Click here to watch a new video exploring the work of the center.

Congratulations, Huw!