Professor Bruce Lipshutz, University of California, Santa Barbara, USA, talks with Dr. Jonathan Rose for ChemistryViews.org about writing a great paper, his amazement of what organic chemistry can do for society, and the challenges of altering the current practice of doing synthetic organic chemistry in environmentally harmful organic solvents.
What got you interested in organic chemistry?
It all started in my 7th grade class with a chair. My chemistry teacher at Riverdale Junior High School in the Bronx, claimed that she could identify the chemical composition of a chair. I wondered how one could know such things at the molecular level!
After being uninspired in high school chemistry, even at the heralded Bronx High School of Science, I eventually landed in sophomore organic chemistry, taught by Howard Alper, who confirmed in an organized fashion that one could know about far more than just a chair. I was enlightened that organic chemistry involved the most fundamental properties of molecules, including the molecules of life. However, it took years to appreciate just how powerful the science of organic chemistry truly is; how it touches just about every aspect of our lives, and how chemists through our discoveries exert an influence on society.
Today, I remain fascinated by what is possible, based on the impressive advances that continue to appear.
What is most interesting for you in organic chemistry?
I am most interested in what organic chemistry can do to change the way modern medicine is practiced from the standpoint of drugs. How can we shift the focus to preventative care, using existing compounds, such as CoQ10 and omega-3s, for preventative purposes. We can make well-designed analogs of these fundamental natural products that could lead to an improved quality of life by keeping us healthier and better able to fight disease – perhaps evolution did not make the best choices.
What do you think are the biggest challenges facing organic chemistry and where do you think it is headed in the future?
The biggest challenge I see is altering the current practice of doing organic chemistry in environmentally harmful organic solvents.
As with most traditionally trained organic chemists, I was taught to problem solve without consideration of the environmental impact of the solutions devised. I never thought about developing SEM-Cl as a protecting group as an Assistant Professor that is utilized in chlorinated solvent, or introducing higher order cuprates that require stoichiometric copper, an organic solvent, and energy to cool the medium. But I do now, because we must recognize that resources are limited, and that we have an obligation to minimize the creation of organic waste in our work.
Green chemistry is in our future.
You are editor of the 4th Organometallics in Synthesis Manual. What kind of impact do you want the book to have?
The 4th Manual, which I oversaw, – as with the previous Manuals – is intended to both broadly educate the reader, and most importantly, to make life easier for the practitioner. It breaks down the barrier for the novice looking for an organometallic solution to a synthetic problem. And for more experienced researchers, it helps to get the reader into an area of organometallics with which he/she might not be so familiar. So much of organic synthesis today involves metal chemistry that it seems almost impossible to know the intricate details of even one metal’s full potential. Hence, these Manuals are like having a personal consultant at your fingertips: pick a metal that does the chemistry desired, and then let the Manual guide you. It offers many representative procedures, and it provides references to the original literature for quick viewing.
Perhaps the most valuable aspect to these chapters is the many secrets behind the success that took years of trial and error by the researchers that have developed this expertise. It’s an invaluable reference that should be on every organic chemist’s desk. Pick any chapter and one can feel the passion behind the prose.
Why do you take the time besides your other commitments to write?
Writing is how we scientists share our thoughts, and our progress. It is how we broadcast our discoveries to the world. How else would we know what others have done, and who is working in which fields? Writing is one of the keys to communication.
Should scientists learn how to write?
Absolutely! I have been inspired through the years by good authors of chemistry. I identified long ago those authors who appeared, at least to me, to have terrific writing skills. And then I evaluated their work for more than scientific content.
Writing a great paper to me means more than having great science; it has to flow, smoothly, easily; and when it happens, you know it. A good article tells a good story. It’s no different from giving a great lecture; the science must be there, but the audience wants more.
What are your interests outside of chemistry, and what do you do in your spare time?
Well, having grown up in The Apple (New York City), I was addicted to playing hoops for most of my life, but after passing 40, those pickup games on campus with eighteen year olds were too demanding. Even Havlicek retired from the Boston Celtics at 36!
So I joined the Y (YMCA) and started to work out, and to jog, and that’s my weekend warrior routine.
Most of my “spare” time had been devoted to raising three children, and now with the “baby” just graduating from Cal, I have started to “get out more”; traveling, wine-tasting, sampling local cuisine, and walks on the beach … all with my fiance, Carol.
Thank you for the interview, Mr. Lipshutz.
Bruce H. Lipshutz gained a B.A. from the State University of New York at Binghamton, USA, before moving to Yale University, New Haven, Connecticut, USA, for his M.A. and Ph.D. He completed his Ph.D. in 1977 under the supervision of Harry Wasserman. From 1977–1979, Lipshutz was a postdoctoral research fellow in the group of E. J. Corey at Harvard University, Cambridge, MA, USA. In 1979, he joined the University of California, Santa Barbara, USA, as an Assistant Professor. Since 1987, he has been full professor at the University of California, Santa Barbara.
Lipshutz’ research looks at new synthetic methods, particularly those for green chemistry, asymmetric catalysis, natural products total synthesis, including coenzyme Q10 and its analogs, and heterogeneous catalysis. Recently this has included mixed metal-supported cross-coupling reagents and homogeneous catalysis based on micellar catalysis to effect transition metal-catalyzed cross-couplings in water at room temperature.
Many of his new reagents and technologies are of broad appeal to the synthetic community and are commercially available, for example, “Higher Order Cuprates”, “Cuprate-in-a-Bottle”, DCAD, “Copper Hydride-in-a-Bottle”, and Ni/C and Cu/C.
Selected Awards
- American Chemical Society (ACS) Arthur C. Cope Scholar Award, 1997
- UCSB Foundation Distinguished Faculty Teaching Award, 2002
- Solvias Ligand Prize, 2003
- Presidential Green Chemistry Challenge Award, 2011
- Encyclopedia of Organic Reagents (EROS), Reagent of the Year, 2012
Selected References
- On the Way Towards Greener Processes, as Quantified by E Factors,
B. H. Lipshutz, N. A. Isley, J. C. Fennewald, E. D. Slack,
Angew. Chem., Int. Ed. 2013, in press.
DOI: 10.1002/anie.201302020 - Organocopper Chemistry,
B. H. Lipshutz,
In Organometallics in Synthesis – a Manual, 4th Edition,
M. Schlosser (Ed.),
Wiley-VCH, Weinheim, Germany, 2013.
ISBN: 978-0-471-984160
DOI: 10.1002/9781118750421.ch6 - Stille Couplings in Water at Room Temperature,
G-P. Lu, C. Cai, B. H. Lipshutz,
Green Chem. 2013, 15, 105.
DOI: 10.1039/c2gc36042j - C–C Bond Formation via Copper-Catalyzed Conjugate Addition Reactions to Enones in Water at Room Temperature,
B. H. Lipshutz, S. Huang, W. W. Y. Leong, N. A. Isley,
J. Am. Chem. Soc. 2012, 134, 19985.
DOI: 10.1021/ja309409e - Rh-Catalyzed Asymmetric 1,4-Addition Reactions in Water at Room Temperature with In-Flask Catalyst Recycling,
B. H. Lipshutz, N. Isley, R. Moser, H. Leuser, B. R. Taft,
Adv. Synth. Cat. 2012, 354, 3175.
DOI: 10.1002/adsc.201200160
