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A New Collaborative Approach For Chemists

C–H functionalization specialists discuss how they’ve spurred once-competitive synthetic chemists to pool their resources

by Huw M. L. Davies , Daniel Morton
October 5, 2015 | APPEARED IN VOLUME 93, ISSUE 39

Chemists representing 23 research groups at 15 research institutions make up the Center for Selective C–H Functionalization.

The field of organic synthesis has undergone a startling shift of emphasis during the past 20 years. The pinnacle of research was once the total synthesis of natural products. Many research groups fiercely competed to be the first to make a particular molecular target. Consequently, the field developed a highly competitive atmosphere, and it was rare to find synthetic organic chemists working together toward a common research goal.

Organic synthesis has now become much more diverse. The current focus is not so much on competition among chemists but on demonstrating the vital role that organic synthesis has on other established and emerging research disciplines. For instance, click chemistry and protein ligation are key in chemical biology, and metal-catalyzed cross-coupling is important to pharmaceutical and materials sciences.

Credit: CCHF
Huw M. L. Davies is the Asa Griggs Candler Professor of Chemistry at Emory University and director of the Center for Selective C–H Functionalization.
Credit: CCHF
Huw M. L. Davies is the Asa Griggs Candler Professor of Chemistry at Emory University and director of the Center for Selective C–H Functionalization.

One of the exciting developments for us is C–H functionalization. This synthetic methodology approaches the construction of organic molecules from a novel perspective. Rather than replacing or modifying reactive functional groups such as alcohols, amines, and carbonyls as was done in the past, chemists have learned how to modify typically unreactive C–H bonds, which are the most abundant functional groups in organic compounds. This strategy leaves the traditional functional groups alone and enables researchers to streamline the synthesis of new types of chemical entities, making reactions more sustainable and less expensive.

Credit: CCHF
Daniel Morton is managing director of the Center for Selective C–H Functionalization.
Credit: CCHF
Daniel Morton is managing director of the Center for Selective C–H Functionalization.

In 2008, we had the opportunity to initiate a new approach for organic synthesis collaboration, which eventually grew into the Center for Selective C–H Functionalization (CCHF), one of the National Science Foundation’s Centers for Chemical Innovation. We had just moved to Emory University and recognized that the rapid development of C–H functionalization would benefit from a broad-based approach involving many chemists and perspectives.

The ultimate goal of the center, which now has a team of 23 faculty members from 15 academic institutions across the U.S., is to further develop selective C–H functionalization so that it will continue to revolutionize the practice and reshape the teaching of chemical synthesis. More than half of CCHF’s faculty are synthetic organic chemists of various flavors involved in methodology development, total synthesis, and applications in the materials and pharmaceutical sciences. Recognizing that this focused expertise was not enough to effectively achieve our goals, we brought in experts from the fields of reaction optimization, chemical engineering, inorganic catalyst design, enzymology, and theoretical chemistry to complement the efforts of the synthetic chemists.

In addition, CCHF has several industrial partners participating in collaborative precompetitive research. Chemical companies, in particular in the pharmaceutical industry, have long forged collaborations with individual academic researchers. But the ability for academic and industrial chemists to work together more openly on basic synthetic strategies before patentable applications are developed is enhancing the translation of academic C–H functionalization research to the industrial setting.

The biggest challenge for CCHF has been to overcome the tight-lipped, head-down approach of organic chemists of the past. We needed to develop a new attitude toward collaboration, one that fosters an atmosphere in which ideas can be freely exchanged and considered while working toward a common set of goals.

Sharing one’s research ideas as they are hatched is always risky. When we started the center, none of the original members had collaborated, and in fact many people would have considered us research competitors rather than collaborators.

We began with a symposium in which all the professors and their students came together for brainstorming, not only on potential research projects, but also on what would be the best practices for effective collaboration. This is now a yearly event.

The center’s members are widely dispersed, so we needed to devise an efficient way for regular communication. This led us to the real backbone of CCHF’s efforts: weekly videoconferences during which 20 to 30 groups discuss their latest results and new research opportunities. We have become so adept at multisite communication that we have expanded our reach and created a global network involving universities in Japan, South Korea, and the U.K. This year we went a step further and began a virtual symposium on C–H functionalization, which was held on July 28. The symposium attracted more than 1,300 participants joining us from lecture halls at several pharmaceutical companies and about 70 universities around the world.

The collaborative, synergistic atmosphere we have created has exceeded our expectations. All CCHF members are stimulated by being among a large community of experts across the chemical spectrum. Students and postdocs are immersed in an environment where they can deepen and expand their knowledge in their individual disciplines. We hope that CCHF will become recognized as a model for how to conduct collaborative research within the field of organic chemistry and indeed all of chemistry.

Huw M. L. Davies is the Asa Griggs Candler Professor of Chemistry at Emory University and director of the Center for Selective C–H Functionalization.

Daniel Morton is managing director of the Center for Selective C–H Functionalization.

Views expressed on this page are those of the authors and not necessarily those of ACS.



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Andrew (October 5, 2015 12:16 PM)
I think it's indicative of the changing times that such a large scale collaboration is even possible in the first place. Really cool stuff.

Any particular challenges that have arisen throughout the course of such collaboration?
Huw Davies (October 6, 2015 1:13 PM)
Andrew, good question!. We needed to spend quite a bit of time at the beginning discussing what would be our expectations of the Center members. We needed to develop a culture of trust where ideas can be shared and everyone is exploring avenues for collaboration.
Simon Blakey (October 5, 2015 1:05 PM)
Been amazing to be involved with. Our ability to utilize 1st row transition metals in catalysis, and to understand what is going on in our reactions has been hugely enhanced by interacting with this large group that have a complementary knowledge set to my own.
Sandeep Raikar, Ph.D (October 5, 2015 1:55 PM)
I am Sandeep Raikar, postdoctoral scholar in Huw Davies' group at Emory University. The CCHF has allowed me to work in collaboration with some of the finest synthetic organic chemists in the world which I would not have thought of, otherwise. The collaboration has taught me a lot and broadened my horizon of thinking scientific problems.
Alex (October 5, 2015 2:04 PM)
I am a member of Professor John Montgomery's lab at the University of Michigan and have been involved with the CCHF or a little over a year now. My efforts have been focused in developing nickel catalyzed C-H functionalization methods. The input gained from others in the center via video meetings and annual site visits are crucial to my success as a researcher. Seeing leaders in the field participating in high levels of collaboration through the center has had a large influence on the way that I approach challenges in chemistry.
Aaron Bedell (October 5, 2015 4:46 PM)
I'm Aaron Bedell and I am a graduate student in the Sorensen lab at Princeton.

My primary project in the Center focuses on the application of chemical methods, developed by other CCHF researchers, in target-directed synthesis. We are looking to demonstrate the power and utility of these enabling disconnections while also continuing to probe their robustness in complex molecular settings. As a result we have forged strong ties and collaborations with with several groups, including the Davies, Yu, Du Bois, and Blakey labs.

Participation in the CCHF has been a tremendous resource for us, particularly in facilitating direct student-faculty interactions and providing real-time access to new research.
Ken Houk (October 5, 2015 5:16 PM)
The weekly video conferences keep informing me and my group regularly about wonderful opportunities for collaboration. We already have collaborations with many groups in the CCHF, but I wish we had time to provide computational input into projects from all the groups!

A comment on the competitive tradition in synthesis: I came from the Woodward group which, at the time, was pursuing Vitamin B12 jointly with the Eschenmoser group. And most of the graduate students were working on the predictions stemming from the fabled collaboration between Woodward and young physical chemist, Roald Hoffmann! So there are celebrated examples of synthetic chemists collaborating in the past, and demonstrations of the fruits and impacts of those collaborations.
Huw Davies (October 6, 2015 1:20 PM)
Ken, you are certainly correct that there have been some wonderful collaborations between synthetic organic chemists but they are relatively rare. It has been more common to see longstanding collaborations between chemists from different sub-disciplines.
Cora MacBeth (October 5, 2015 6:16 PM)
The graduate students and post docs within the CCHF have also benefit from this unique training/research environment. Instead of working with one PI, they get the opportunity to know a number of of PIs from a variety of institutions and interact with them on a regular basis. The students and post docs have also adopted a collaborative spirt and often take the lead spearheading these interactions.

The involvement of our industrial partners has also benefited our students and post docs a great deal. These partners have dedicated a great deal of time and energy into developing professional development programming that helps our students and post docs understand the industrial job market in STEM fields and how to be competitive in this market.

David H. Sherman (October 5, 2015 6:42 PM)
The collaborative culture within the CCHF has offered game-changing new directions in my own research program relating to engineering of C-H oxidation biocatalysts. The opportunities to interface with experts in computational chemistry, and awesome synthetic chemists has shown the deep complementary opportunities with a broad range of research programs.
Julian West (October 5, 2015 7:37 PM)
I'm a 3rd year graduate student in the Sorensen group working on cooperative catalysis with base metals. Having been a member of the CCHF since my first year, I must say that the benefits to my science and professional development have been enormous.

Indeed, it has been our involvement in the Centre that inspired my project and a major portion of our group's focus going forward. This direction has been honed and refined through discussions facilitated within the CCHF, which provides a safe space in the video conferences and annual meetings to discuss unpublished results and to get genuine feedback from some of the biggest names in the field and, when the time arises, an open avenue for collaboration!

The professional development benefit is no less impressive: presentation skills are sharpened through presenting at the well-attended video conferences and in-person talks and posters at the annual gatherings. Students and postdocs are provided the valuable opportunity to network not only amongst themselves but, also, all the faculty and industrial partners participating in the Centre. Our expansive education, outreach, and diversity component (coordinated by the talented Dr. Monya Ruffin) further provides students, postdocs, and faculty with the ability to really engage underserved groups and the greater public through a dizzying array of thoughtful activities and initiatives.

All in all, if one wanted to chart my own development, as both a graduate student and member of the the chemistry community, since joining the CCHF, I think that they would find the slope difficult to measure from being so steep. The Centre produces both top-notch science and scientists and I think that it provides a valuable template for how organic chemistry can continue to thrive in the modern era.
Christopher Jones (October 5, 2015 8:52 PM)
As chemical engineers working with this amazing group of organic chemists, my group members and I have benefited immeasurably from the interactions with experts in organic synthesis. The skills learned by the students and postdocs - synthetic chemists learning to work and communicate with process-focused engineers and vice versa - nicely foreshadow the types of interactions they can expect as practicing chemists and engineers in industry.
Eric Moschetta (October 12, 2015 10:22 AM)
As one of the postdocs working in Prof. Jones's lab, I have dramatically improved my knowledge of state-of-the-art chemistry and how to incorporate these technologies into continuous flow processes. I am grateful for the experiences in collaborating with a number of different groups in the CCHF because I am able to diversify my skills as an scientist and share my skills with others.
Liangbing (October 5, 2015 10:29 PM)
These collaborative activities are really beneficial, not only to members in the center, but also to chemists nationwide, even worldwide.
Richmond Sarpong (October 6, 2015 10:56 AM)
The CCHF center has been such a stimulating environment for me and for my group to learn about the latest cutting edge methods for C–H functionalization that we can utilize to implement our strategies for the preparation of complex molecules. In fact, many technologies available through the center can be accessed by the general public from the center website!
John Gipson (October 6, 2015 11:12 AM)
I work in Matt Sigman's group at the University of Utah developing catalyst for C-H hydroxylations. The CCHF has provided a great opportunity for interacting with many other groups across the nation both in our weekly video conferences and in person during our annual meeting. Additionally, I've had the privilege of working with Professor Justin Du Bois and his group at Stanford in our efforts to develop new catalyst for selective C-H functionalization and in understanding the mechanisms. This new model for collaboration within chemistry has the potential to make greater strides within the science community.
Brett McLarney (October 6, 2015 11:26 AM)
As a graduate student in the France Lab at Georgia Tech I have been a member of the Center for two years now. The pace with which the Center develops chemistry is blazing and stems, without doubt, from the collaborative paradigm permeating its network. Being a part of such a transformative group is highly motivating and feels truly special.
Brian Stoltz (October 6, 2015 5:25 PM)
Our group has been working collaboratively and enthusiastically with a number of laboratories within the center in the C-H functionalization area. The CCHF has been a wonderful source of knowledge, depth, and breadth in this relatively new area for synthetic chemistry. It has been fun to interact with groups that we typically or otherwise would not have, and to learn about their expertise and perspectives. I am looking forward to a day when C-H bond are truly regarded as groups that can be manipulated in synthesis at will in the same way we work with other functionality. I believe that the CCHF is helping to pave that way!
Seth Ahlquist (October 6, 2015 5:31 PM)
My name is Seth Ahlquist and I am a research associate in the Houk Lab at UCLA and an inaugural CCHF CSURP Fellow. My work in the Center has been a collaboration with the Jin-Quan Yu Lab at The Scripps Research Institute where my project seeks to explain the mechanism of their cutting-edge Template-Directed C-H Functionalization synthesis methodology as well as computationally guide the design of new substrates for these reactions.

The synergy of the research groups in the CCHF is truly remarkable and constantly results in new approaches and ideas for future experiments. Additionally, I believe the Center offered me an unmatched experience as an undergraduate student with extensive opportunities for personal development through performing original research, presenting my results, and experiencing excellent mentorship.
Cecilia Tortoreto (October 6, 2015 7:04 PM)
The collaborative network within the center favors the cooperation between a broad range of chemical disciplines, providing means to address challenges and problems that it would be impossible for single groups to consider.
Students and postdocs have the unique chance to become part of a large network of collaborators and gain a great experience of leading collaborations between research groups. Additionally, students gain broader skills by being involved in the various outreach activities of the Center. As a postdoc, it is highly motivating for me to be involved in this exciting team and I have the opportunity to gain the skill sets to be well-prepared for my future career.
Colleen Scott (October 6, 2015 9:45 PM)
The center is also a great source for mentoring; not only graduate students and post-docs, but also Assistant Professors at other research institutions such as undergraduate and underrepresented institutions. This is extremely beneficial to those Assistant Professors who now have the opportunity to connect with several senior Professors from top research institutions and develop collaborations that would probably never happen without the center. Kudos to CCHF :-)
Colleen Scott (October 6, 2015 9:47 PM)
The center is also a great source for mentoring; not only graduate students and post-docs, but also Assistant Professors at other research institutions such as undergraduate and underrepresented institutions. This is extremely beneficial to those Assistant Professors who now have the opportunity to connect with several senior Professors from top research institutions and develop collaborations that would probably never happen without the center. Kudos to CCHF :-)
Colleen Scott (October 6, 2015 9:51 PM)
The center is also a great source for mentoring; not only graduate students and post-docs, but also Assistant Professors at other research institutions such as undergraduate and underrepresented institutions. This is extremely beneficial to those Assistant Professors who now have the opportunity to connect with several senior Professors from top research institutions and develop collaborations that would probably never happen without the center. Kudos to CCHF :-)
Ben Wertz (October 6, 2015 11:32 PM)
As a first year Ph. D. student working with the CCHF at Emory, it's very exciting to have such a great opportunity to do meaningful research with big implications for how chemists think about building molecules. Starting a graduate program in chemistry is certainly stressful, but knowing that there is significance to my work and being surrounded by such talented individuals is extremely motivating.
Seth Marder (October 7, 2015 10:03 AM)
As a materials chemistry the opportunity to work directly with people developing catalysts and new methodologies has greatly expanded my capacity to design materials and synthesize them efficiently. As a mentor, the opportunity to have my students participate in the centers various programs, has been very exciting. This year for example, two of my students were able to spend about 10 weeks in Korea working with a top synthetic group, learning chemistry that I would not be able to teach them. In addition, I have been able to develop new personal relationships with excellent people throughout the US and the world, facilitates by the Center. I have long been a fan of collaborative research centers and it is nice to seen the organic chemistry community embracing and benefiting from working in a center mode!
Eric Voight (October 7, 2015 4:08 PM)
As an industrial chemist from AbbVie participating in a pre-competitive research project with the CCHF, I have been thrilled with the degree of collaboration exhibited among the CCHF research groups and industrial partners. We have only scratched the surface of what may be possible through this unique research environment. The opportunities we have had to engage with top researchers in the field of selective C-H functionalization have been spectacular.
Junxiang (October 7, 2015 5:37 PM)
As a member from the materials subgroup, I benefit a lot from CCHF. We've made some organic materials with the interesting opto-electronic properties by using CH activation, in a strongly collaborative manner within different groups. CCHF provides us not only a platform to brainstorm new ideas, but also a place to share intermediates, which accelerates our research substantially.
Robert Buntrock (October 9, 2015 4:06 PM)
The schools involved are shown on the map and several members of some of the research groups have commented but I'd appreciate a list of the 23 research group leaders at the 15 schools.
John Gipson (October 10, 2015 3:38 PM)
You can find bios of all the members of the center on NSF-CCHF website. Here is a link to the faculty members involved
Kuangbiao Liao (October 10, 2015 12:46 AM)
Joining the center is one of the criticle part in advancing my research career. There are so many talented peers and PIs, either their research or their comments on my project are very useful in improving my understanding and knowledge in C-H functionalization. The communication way, such as video conferrence, is very efficient and convenient.
Jinquan yu (October 10, 2015 4:35 AM)
Our collaborations with strong synthetic groups have put our reactions to test and more than often raised the bar for developing more robust CH activation reactions. Our collaborations with mechanistic groups including computational and kinetic studies has led us to look at places not obvious to us before.
Jamal Musaev (October 10, 2015 10:43 AM)
I am Jamal Musaev, member of the Center’s Governance Committee and its one of co-founders.
Success in high risk and transformative science, such as stereoselective C-H functionalization, requires multidisciplinarity and true collaboration between the scientists with different scientific backgrounds and relies on the atomistic level understanding of intimate details of the problem. Such approach complements novel synthetic approaches, opens new horizons for predictive and atom-efficient synthesis, and guide selective C-H functionalization strategies. Center Stereoselective CH Functionalization (CCHF), in particular, and center-ness platform, in general, is an ideal to promote truly collaborative culture and multidisciplinary education and research. Established true collaboration and trust in CCHF between the synthetic, computational and advances us on designing of sustainable, green and highly selective C-H functionalization reactions with low-catalyst loading, and utilizing earth-abundant first-row TM catalysts, and even non-TM catalysts.
Michael Gilbert (October 10, 2015 11:56 AM)
The collaborative environment within the center is fantastic. The opportunities to work with colleagues both locally and across the country has greatly enhanced our understanding of directed enzymatic oxidation. Even groups that are not directly involved in this project in the center freely contribute valuable suggestions during vidyo conferences and annual meetings.

From the viewpoint of a student, the ability of such a diverse group of chemists to set aside competitive tendencies and work together towards a common goal has forever changed my view on the nature of chemical research.
Kelly Kim (October 10, 2015 2:29 PM)
I'm a graduate student in Brian Stoltz's group at Caltech, where I work on late-stage C-H oxidation of complex molecules in collaboration with Justin Du Bois's group at Stanford. I've been involved with the CCHF since 2012, and it has been a truly wonderful experience. The weekly videoconferences and annual meeting are great sources of motivation and fresh ideas for the science, and my favorite part has been getting to meet and chat with all the students, postdocs, professors, and industrial collaborators from across the CCHF. By connecting people from across the country (and also across the world), the CCHF does a great job with facilitating discussions and collaborations amongst scientists who may otherwise not have interacted. Additionally, the professional development sessions for students and postdocs are great resources and useful in planning for next career steps. Overall, I'm very glad to have had the opportunity to work with all the fantastic people in the CCHF!
Noam Levi (October 11, 2015 5:39 PM)
I am a postdoctoral fellow in Andy Borovik’s group at UC-Irvine working on first row metal catalysis for various C-H transformations. For a field that incorporates many aspects of organic and inorganic chemistry, the center holds a treasure of people from various disciplines of chemistry and provides open communication mostly through the weekly video meetings. The center affords great collaborations opportunities, discussions and eye-opening questions and inputs otherwise not possible.
Brunelli (October 11, 2015 10:57 PM)
The diversity of research encountered in the center inspired new creative endeavors to collaborate and challenged all members to become better.
Larry Hamann (October 23, 2015 9:48 AM)
The opportunity to collaborate in a pre-competitive manner from the earliest days of inception of the center has been incredibly valuable to us in addressing research challenges in C-H Functionalization of common interest to academia and pharma. The breadth of our ongoing collaborative projects truly reflects the wide-ranging applications of C-H methodology, and the level of intellectual engagement from so many faculty, graduate students and post-docs has been creatively catalytic.
SPANDAN CHENNAMADHAVUNI (October 23, 2015 3:00 PM)
I am Spandan Chennamadhavuni, postdoctoral scholar at Emory University. It was amazing experience to be part of 6th Frontiers in C - H functionalization symposium at Emory. Being an Alumni of Prof. Huw Davies's group, it was fascinating to see so many world-class synthetic organic chemists coming together under one roof, to brainstorm to tackle next generation synthetic challenges. I am particularly intrigued by interdisciplinary science that is being performed in the center and its application in pharmaceutical industry & material science. Its outreach activities needs special applause for seeding interest for chemistry in young budding minds of children in the schools. I wish all the very best for the center and its members. I hope it attracts more Industry partners in the near future.

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