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Arthur C. Cope Award Winner: Stephen L. Buchwald

by Bethany Halford
March 4, 2013 | A version of this story appeared in Volume 91, Issue 9

Credit: Bachrach
Stephen L. Buchwald
Credit: Bachrach

Were it not for the work of Stephen L. ­Buchwald, synthetic chemists would have a much tougher time assembling agrochemicals, novel materials, and, in particular, new drug candidates.

“There’s a saying in big pharma that I hear quite often: ‘No Buchwald, no drug.’ And it really is true,” says Phil S. Baran, a synthetic organic chemist at Scripps Research Institute, in California. “His impact goes beyond the relatively small academic universe and penetrates the vast industrial audience in ways that are truly enabling and inspirational to others. It is clear that his science is unlocking opportunities in every small-molecule program in drug, agrochemical, and materials research.”

Buchwald’s work “has led to some of the most widely used reactions in the world,” adds Eric N. Jacobsen, a synthetic organic chemist at Harvard University. “It is no exaggeration to say that every major pharmaceutical company practices this chemistry on a daily basis in their discovery groups.”

Research in the Buchwald lab involves the discovery and development of new ways to make carbon-carbon and carbon-heteroatom bonds, with a strong emphasis on cross-coupling chemistry. “No chemical methodology has had a greater impact over the past decade than cross-coupling, and no chemist has made greater specific contributions over that period than Stephen Buchwald,” Jacobsen notes.

Buchwald’s group developed the first general method for making aromatic C–N bonds via cross-coupling. Buchwald was also behind a family of palladium pre­catalysts that circumvent difficulties with induction times and the erratic behavior commonly associated with cross-coupling catalysts.

“He made seminal efforts in developing a family of biaryl phosphine ligands for palladium cross-coupling processes that have enabled the advent of C–N bond-forming reactions that are so robust and generically useful that they have transformed the practice of drug discovery and production,” adds David W. C. MacMillan, a synthetic organic chemist at Princeton University.

Students of nomenclature will note that those ligands have brought a measure of fame to the graduate students and postdocs who helped create them. DavePhos, BrettPhos, and JohnPhos all bear the names of the Buchwald lab members who first synthesized them. Buchwald’s cats also have been immortalized with the ligands RuPhos, RockPhos, and TrixiePhos. Buchwald says he gets many of his best ideas from his cats, particularly from Rufus.

“My philosophy is that if you’re going to develop something that somebody else is supposed to use, then you’d better listen to what they say about it is important to them,” Buchwald says. “Because of my consulting work in the pharmaceutical industry, I can see what gets used—what is a contender and what is a pretender.” For example, he says, chemists working in drug discovery tell him they’re interested in heterocycles and reagents that aren’t air sensitive.

Buchwald, 57, attributes his success to two things: luck and working at Massachusetts Institute of Technology, where he is currently the Camille Dreyfus Professor of Chemistry. “You can’t overemphasize how advantageous it is to be at a place like MIT,” he says. “You have all these really smart, enthusiastic coworkers, and whenever you get full of yourself all you have to do is talk to the person next door to you who has won five times more awards than you have. It’s easy to be kept relatively humble.”

Buchwald says he’s very excited to be this year’s recipient of the Cope Award. He and Cope have a few things in common: Cope was on the faculty of MIT for more than 20 years, and Buchwald has spent his entire faculty career at the institution. Both are also natives of Indiana, and Buchwald says anyone who was to look at his Internet browsing history would see evidence of his ongoing fanaticism about Indiana University’s basketball team (he confesses to visiting the team’s website at least six times a day).

Buchwald got his start doing chemistry research at Indiana University with Gary Hieftje as part of a summer science program for high school students. He also credits his high school chemistry teacher, William Lumbley, for sparking his interest in the subject. Research also figured heavily into Buchwald’s life as an undergraduate at Brown University. He conducted research there with both Kathlyn A. Parker and David E. Cane, who instilled in him the love of organic chemistry. He also spent a summer at Columbia University working with Gilbert Stork, who remains one of his heroes.

Buchwald did his doctoral research under the aegis of Jeremy R. Knowles. He was a postdoctoral fellow at California Institute of Technology with Robert H. Grubbs before joining the faculty at MIT in 1984.

Buchwald says he has always enjoyed the support of his parents, wife, and children. “My wife works twice as hard as I do, and she’s a saint. My kids are great. My family keeps me well grounded.”

When Buchwald isn’t thinking about chemistry or Indiana basketball, he likes to read mystery novels. He admits that his collection is “ridiculous” in size, made up largely of used books. He half-jokingly says he plans on sending the collected works of the author he’s currently reading, Quintin Jardine, to his old mentor and fellow mystery fan, Bob Grubbs.



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