Earlier this month, organic chemist Ei-ichi Negishi died at the age of 85. I missed this event (I wasn’t posting during those few days) so I wanted to note it here, because Negishi was a huge name in the field. There’s a Nobel prize to back that statement up (Chemistry, 2010), and plenty of other awards as well. But si monumentum requiris, circumspice: the sorts of metal-catalyzed couplings that he spent his career working on have become indispensable tools in organic synthesis, and the field is still an active area of research. Carbon-carbon bond formation is a high-denomination coin in organic chemistry, as are high-turnover catalytic methods, so the amount of interest (both academic and industrial) in these reactions is not surprising. The number of compounds that have been made by now through these routes is just not feasible to even start counting.
As his Chemistry World obituary notes, Negishi actually left a press conference about his Nobel award to go teach a sophomore organic class, and I don’t think anyone who knew him well would be surprised to hear it. He had a legendary work ethic (retiring from Purdue, where he spent nearly all his career, only two years ago). Interestingly, he had been a postdoc with H. C. Brown, who later was Purdue’s first Nobel winner. That work ethic extended to his lab – stories I’ve heard over the years made clear that Negishi expected people to be at the bench solving problems, and his field of research gave them plenty of opportunities. At the same time, he also had a reputation for approachability, for students of all levels, and shared his expertise freely at all times.
The metal-catalyzed coupling reactions have been developed to the point where it’s hard (read: impossible) to keep track of all the possible reactions, conditions, and substrates. There are a lot of variables that can be explored, and the detailed mechanisms of the reactions can change on your depending on the metal used and many other factors besides. But when optimized, they can be run on very large scale in a reproducible way. My own graduate training in the 1980s took place when this sort of thing was just starting to come into better focus, and it really did seem like having some sort of magic powers to be able to form all these compounds through stitching together actual carbon-carbon bonds. Organic chemistry students now come up in a world where these things are facts of life, but that Nobel (which also went to Richard Heck and Akira Suzuki) was well-deserved and frankly, well overdue. One of things that might have delayed it was the 3-awardee-maximum requirement; there were many others who had made serious contributions to the area, because it was such a huge field to work in.
No Nobel since has been awarded for new synthetic organic methods. We’ll see another one eventually, but by the time it happens none of the living Nobel winners in that field may still be with us.
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